Boron annual survey covering the year 1980 Part II

199

BORON ANNUAL

SURVEY

COVERING

THE

YEAR

1980

PART II Kurt

Niedenzu

Department

of Chemistry,

Lexington,

Kentucky

University

40506

of Kentucky

(U.S.A.)

CONTENTS 1 Reviews

2 Some

and Books

Data

3 Hydridic

of General

Interest

200

Species

201

4 Triorganylboranes

202

5 (0rganyl)haloboranes

206

6 Boron-Oxygen

Compounds

7 Boron-Sulfur

Derivatives

8 Boron-Nitrogen 9 LEWIS

11 Metal

Acid

Complexes

208 214 215

and Related

Borate(l-)

Materials

221

Species

223

Derivatives

REVIEWS Boron

226

and Related

AND cage

compounds (141),

of recent

status-of

(llO),

boron

as ligands

are the topics

Aspects

229

BOOKS

complexes

theterocycles

present

Adducts

and

12 Physiological

metal

and Boric

Compounds

Acid-Base

10 Boronium(l+)

1

199

carboranes

subhalides

in transition reviews.

phosphaneborane

including

(2621, metal

A brief

and boron

chemistry

accounting

chemistry

Previous survey .see:J.Organ&etal. Chem:, Vol. 196

their

has also

(142) of the been

1 - 35.

200

presented been

(245) and the NOBEL

published

(235,

A new book chemistry; boron

compiled

(66)

contains

in biology,

by KLIEGEL

to a uniform

dealing

literature

to the original

2

SOME

OF GENERAL

the B6 ring

isolated

from

of ClB(N(CH containing

been

updated

and

restricted

concentrates

position.

as

on the

is guided

A formula

parts

(144).

by the

index

is

of the volume.

INTEREST boron

derititive

species

of general interest

compounds

(-BN(GH3)2-)6s residue

which

~211 be

of the dehalogenation

A study

compound

porphin.

BsS16,

S8 in vacuum bridged

(130);

by S groups

structure.

of 'H and l3 C NMR

spectra

(28) is principally

findings

of an earlier

Previous

comparisons carbon-13

ions have

boron(l)

An inorganic

of B S with 23 of four B2S3 rings

consists

the type C6HsBX2

with

and the first

by fusion

into a macrocyclic

benium

have

of the end of 1977

of presentation

electron-deficient.

obtained

the molecule

boranes

volumes

distillation

boron

is not

has been

compounds

of the

) ) with Na/K alloy (128). The cited compoundp 322 the B6 ring in chair conformation, is the first

homocyclic that

the

of

has been

Series

is somewhat

of the three

New and interesting include

and pharmacy

date

coverage

of the last

in the last

DATA

of bqron-nitrogen

on the application

Supplement

boron

the order

aspects:

compiled

medicine

closing

compared

principle

treatise

with

the literature

GMELIN

survey

of the New

However,

inorganic

a brief

has

(188).

The 20 volumes GiWELIN Handbook

by H. C. BROWN

240).

and an exhaustive

compounds

Lecture

been

more

in consonance

exhaustive

of boron-11 chemical

of phenylboranes

investigation

chemical shifts

re-examined.(93)

with

shifts

of the

(29).

of .trigonal

of isoelectronic

car-

. The observe&.-trends

201

allow

for a correlation

pi-delocalization reflection

in carbenium

of structural

Also

values.

of pi-bonding

chemical

orbitals

(198).

MNDO of various

types

including

spectra

frequencies

of other

prediction of boron

of heats compounds

for redistribution For a new Semploying f : see (133);

using

of general

HYDRIDIC

interest

of boron

of alcohols

been

the

An empirical reactions

energy

terms

developed

(58).

determination

of boron

pentaborane(9)

proceeds

lwhich can then with

in geological

may be a report

describing

A and Y zeolites

on their

catalytic

and a

activity

(55).

indeed

reaction

of.alkynes

via alkenylated

to small

diarylcuprates

the resultant

monoorganylboranesused

catalyzed

be converted

lithium

(216);

.~a230

of boron

SPECIES

The transition-metal

References

has also

of boron-containing

of the effects

has been

predict

(242).

in the dehydration

boron

or

interaction

spectrophotometric

see

the synthesis

reacts

(247) : correlated

to assign

nonbonded

equilibria

B(CH

and redistribution

for the determination

Also

3

with

compounds

) 3 3’ observed spectra

such as vinylborane.

of formation

atomic

4-(p-sulfophenylazo)-i,8-dihydroxynaphthalene,

materials,

study

used

theory

on 28 boron

such as HBO,

corrections

were

species

performed

a

shift

gauge-invariant

correlations

led to estimate!s! of group vibrational

been

and

illustrate

is a semiempirical

species

and

compounds

in the chemical

utilizing

have

(CH~)~B~H&,

oci3~~ and

interest

shifts

Calculations

and also

parameters

of general

of boron

ions

in boron

mixtures

can be separated.

for the hydroboration

pentaboranes,

carboranes

by transfer

with

(210).

Diborane

of phenyl

of triarylboranes

to

and

Monoisopinocampheylborane of phenylated

tertiary

olefins

(155);

bonded

to the

convenient

and

1,4-oxathiane-borane

sulfur

atoml)

hydroboration

Boron-11

NMR

1,3-butadiene

data

(183).

hydroboration

triple

aminoborylpolyynes,

has been

4

of 3-methyl-

3-methyl-1-boracyclopentane several

as an

intermediates

could

in the

be identified

by

orbital

bonds

studies

examine

in borylpolyynes, (n = 1 to 4)

the inter-

H(CsC),BH2,

and

(181).

of cis- and trans-1,2-dimethyldiborane(6)

examined

temperature

the hydroboration

H2N(CsC),BH2

structure

as a new and

(184).

molecular

throu&h

suggested

being

(15).

of 1,5-cyclooctadiene

Ab-initio

The

via

Similarly,

llB NMR measurements

action

reagent show that

proceeds

intermediate

has been

(with the boron

by gas-phase

electron

diffraction

at room

(234).

TRIORGANYLBORANES Thexylchloroborane,

from

thexylborane

(cH~)~HC--C(GH~)~-BHC~,

and HCl

hydroboration/alkylation diorganylboranes with

(209).

of ketones

Originating butadiene, and

some

route

stepwise

has been

compounds

have

compound

for the

developed

been

and

has been

with

studied

(thexyl)of alkenes

as a general

(127).

determined

developed

elsewhere

obtained

(124).

prepared

(123).

of 1-boraadamantane

been

propargyl

3-methyl-1,2has been

is described

synthesis

has also

been

and tris(2-methylallyl)borane

triallylborane

mixed

hydroboration

triallylborane

of its properties

l-boraadamantane ether

to yield

in a

(232).

from

to the cited

complex

The

can be employed

4,4-dimetnyl-1-boraadamantane

a new method

also

sequence

thexylchloroborane

synthesis

in ether,

obtained

(125) and and its 3,+Dimethyl-

from propargyl (126).

methyl

The reaction

tetrahydropyranyl

Another

ether

of has

203

Condensation occurs

of triallylboranes

by addition

position

0 K,H&

-a- CH&

A new

=

synthesis

reagent

synthesis

with

e

triallylboranes

additional

derivatives

derivatives

derivative

was utilized

react

of the.SnCbB

oxidized

could

R3Si-CHR'-BR$ with

be identified

metallic

in pure

the tin via an enyne

by NMR

these

potassium

Reduction

R.eferenees~_ 230

C6HgB(-CC6Hg="C6Hg-)2,

state

(217).

Reduction

in tetrahydrofuran

of FB(-CCH3=CCH3-)2BF

the

alkyls

spectrocopy. of the general of

can then

be

to alpha-hydroxyorganylsilanes.

synthesized

dia&on.

aluminum

with

to

of which

on interaction

(193)1

(82).

access

derivatives

are formed

trialkylboranes

Pentaphenylborole,

with

(CH3)2SnH2

yield

proceeds

Alpha-silyl-alpha-borylmethane

Li(R3SiCHX)

with

with

of B(i-C3H7)3

(CH3)3SnCsC-CsCSn(CH3)3

structure

of the

for the

heterocycle,

can be B-alkylated

which

on

(268).

or alcoholysis

The reaction

intermediate

Reaction

of I-stanna-4-bora-2,5_cyclohexadienes

transamination

or t-CqH9Li.

is based

or alkyldiallylboranes, (267).

alkoxyacetylenes

Subsequent

alkoxy

and

fashions

of Z-alkoxy-lp4-pentadienes

of allylacetylenes

formation

in the beta

Triallylborane

(122).

(Dialkylamino)dialkinylboranes under

fragment

of allyldialkylboranes with

I-alkoxypropynes

in the following

-20°C

COCHB

respectively,

group

interact

the interaction

latter

of the diallylboryl

to the alkoxy

l-methoxypropyne

with

has been

of the produces

with

species the

metallic

204

potassium

proceeds

of one electron is removed

yields

studies

derivatives esting

the unstable

investigation with

pyridine

the presence

of iodine

the formation

of ate

of B-substituted (24);

studies

steric

acetic

(35);

acid

derivatives to yield

with

the generation

dialkylboranes

dicyclohexylborane,

from

undergo

reaction

of 9-borabicyclo(3.3.l)nonane and

(3.3.l)nonanes

halides

in homologation

1-boraadamantane adamantanates

acetyl

(194).

The latter

with

B$t-CqH&CH3

representatives

have

stabilization the boron

and

crosson the

representative

of 9-alkyl-9-borabicyclo-

Lithium

alkyls

lithium

via

react

with

l-alkyl-l-bora-

can be converted

to 7-

by treatment

chloride.

The first boranes(4)

alkenyl-

studies

methylene-3-alkyl-3-borabicyclo(3.3.l)nos with

reaction

from

of organylboranes

in !MiF'to yield (246).

their

species

(22); kinetic

the employment

carbonylation/reduction

(271)s

methoxyallene

stereospecific

with

(190);

ethylenes

+borabicyclo(3.3,1)nonane

coupling

alkenes

and

in

I-alkyl-1-methoxycyclopropanes

which

allylic

(212);

vinyllithium

lithium

of alkenylcopper

derived

(90); a 13C NMR

trisubstituted

complexe s from

to give

some inter-

requirements

and B-alkyl-9-borabicyclo(3.3.l)nonanes with

F-

of 9-borabicyclo(3.3.1)-

of increasing

of B-alkyl

then

(B(-CCH~=CCH~-)~B)-.

complexes

spectroscopic

the reaction

anion;

the dehalogenated

examination

of the interaction amines

acquisition

9-borabicyclo(3.3.1)nonanes

and 13C NMR and their

Initially,

radical

to yield

employing

photoelectron

nonane

(109).

of a l,@-diborabenzene,

a "B

include

steps

by the potassium

radica-1 anion New

in two

been

described

is achieved

of stable (li2).

by attaching

and the following

species

tetraalkyldi-

In both t-butyl

were

(2);

the

groups

describeda

(1), B2(t-C~H9)2(CH2-t-C4H9)2

B2(t-C4H9)3(CH2-t-C4H9)

cases

(2)~

to

205

The application continues

to receive

of trialkylboranes provides

wide

with

a convenient

reaction

(149);

of organylboranes

effective

ready

molecules

into

alkyl

of organylboranes

with

(16). The palladium-catalyzed of l-alkenylboranes

bromides

gives

and lead(IV) one-pot

acetate

synthesis

with

acetates

react

with

palladium

acetate

stereoselective cross-coupling provides dienes

manner

has also

peroxide been

has been

studied

phenylacetylene has been

Lithium with

with

stabilized

(l-Halo-lacetate

to yield react

derivatives

organic

in

halides

synthesis

of 1,4-

stereochemistry

of the

of organylboranes

to alcohols

(231).

(42), and the

described

by an adjacent

reactions

from

however,

unhindered

acetals

and formals

alkylation

of

of organyl-

(146).

derived

the corresponding

with

stereospecific

by electrochemical

enolates

relatively

The

of organylboranes

triorganylboranes;

evidence,

with

for the

(89).

stereoselective

The methylcopper-induced

oxidation

studied

The reaction

boranes

method

and monoolefins

molybdenum

olefinic

of alkenylboranes

a convenient

and

1-alkyne

and alkenylboranes

to give (172).

with

lead(IV)

l-halo-1,2-dialkylethylenes(li'l),

organic

and allylbenzenes

(148).

with

KCN

or benzylic

of trialkylboranes

of enol

(211);

labelled

allylic

is a new and regio-

alkenyl)dialkylboranes

iodides

but

cross-coupling

to 1,4-alkadienes

and the reaction

is a mild

of 13C or 14C into

introduction

access

reaction

l.l-dialkylethenes

trialkylboranes

of alkenes

reaction

(150).

example,

to symmetric

of ICl with

conversion

For

synthesis

1,2-dimethoxyethenyllithium

route

and the cyanidation permits

attention.

in organic

ketones

based

do not

on 'H and

potassium-enolates triorganylboranes boron

atom

have

interact llB NMR

do react !33).

been

Carbanions

prepared

206

in good

yield

of the type C2Rs

by proton

R2B-CNR'R"

with

from

R = mesityl

base-induced

to carbon

and R', R" = H, CH3,

manner

with

Triorganylboranes, moieties

of an alkyl

respect

are reduced

of methylborylene, for the preparation

to acetylenes

proceeds

C-H bonds

and in ferrocene

has been

studies

on the dynamic

via a radical

A "B shown

that

with

CNO or CNN

13C! NMR

the mesityl

rise

in benzenechromium observed

to replacement The mass

stereochemistry see t-butyl

atoms

(153).

of H by CH3

been

5

examined

and

The

do

has

to the

displacement

shift

gives of the

is insensitive

(31).

some

complexes

of their

of (3-amino-

derivatives

have

(121).

(0RGANYL)HALOBORANES Alkylbenzenes

situ) with

the chemical

of the inner

propyl)dialkylboranes

of Y-

hydroperoxide

are insensitive

in (dimesityl)benxylborane

spectra

(224).

of (dimesityl)methylbore but

(225).

of (dimesityl)alkylboranes

carbon

hydrogens

atom

employed

(26).

study

to an alpha-effect

alpha-carbon

addition

(135). The

character of the alkyl group (31). Sequential of the methyl

whereas

(116). Hypochlorites

mechanism

triorganylboranes and

(23).

of 1,4-diboracyclohexa-2,5-dienes

of tripropylborane

oxidize

group

has been

mesityl-9,10-dihydro-Y-boraanthracenes, degradation

predominantly

organic

to the NN moiety

3

some

from boron

R and BR2 units,

of CH Bx into

and insertion tricarbonyl

occurs

with

of the

CB3B:,

group

to the leaving

interact

BR3P

in a 1,3-addition

groups

For

migration

in a gamma-acetylvinylborane

in an anti

not

dimesitylboranes

(32). The

NNO

abstraction

to yield

react

a mixture

the elimination

with

dihaloboranes

(generated

in

af m- and p-alkylphenyldih~loboranes

of hydrogen

(258).

207

Hydroboration haloboranes

gives

some

unusual

have

been

with

dimethyl

ready

trends

access

and

and

effects.

dienes

employing

borane

hydroborates

directive

monochloroborane,

diborane(4) those

of B4C14

(106);

oxidation

borane

and

products

are

a convenient is

and

of some cyclic

(60).

Thexylchloro-

stereoselectivity

E2C12(t-C4Hg)2

3

or

the

with

as

of

or B2(N(CH3)2)4

on treatment

BCl

as well

(I). The B-B bond

such as B2Cl4 cleaved

of alkynes

(248).

described

are

reactions

steric

excellent

derivatives

derivatives

the

(20): the reagent

see

thexylalkylchloroboranes

B2Br2(t-C4H9)2 have been

and

chloramines

respective

amino-

diborylamine.

Acetoxydifluoroborane of cyclobutene

H2Az,

presents

to both

with

in

hydroboration

For the hydroboration

The diborane(4)

acetic

effects

is sensitive

alkenes

sulfide-di-

to (alkyl)dihaloboranes:

of (alkenyl)dibromoboranes

electronic

also

dimethyl

sulfide-dibromoborane

selective

to afford

with

(19). Similarly,

studied

preparation highly

of alkenes

acid

(185).

reacts

to from

has been utilized

The 111 molar

with

azines

crystalline

FBAz

adduct

containing species

for the acylation of BF3 with

active

hydrogen,

(330).

For some comments on the symmetry group of methyldifluoroL of the adiabatic electron Iborane, see (174). For measurements [affinities of various trihaloboranes (including unsymmetrical I i species), see (69)8 the resultant values are used to obtain IB-N bond energies for the adducts of the haloboranes with f ~trimethylamine. The formation of HJ3Cl2 has been observed !when a E3C13/H, misture laser

is irradiated

(11). For correlation

- boron

isocyanide,

of X2BNCS detailed

(X = Cl,

see

Referencesb.230

a pulsed

of the pair

(78). For the vibrational

Br, I) and C12ENC0,

spectroscopic

,see (241).

effects

with

study

see

CO2

boron

cyanide

spectra

(-75); and for a

on (cyclopropyl)difluoroborane,

208

The photoelectron been and

compared

spectrum

that

with

the one-electron

reduction

(168).

has been

studied

compound

is short-lived.

potassium,

a secondary

identified

as

6

BORON-OXYGEN

allyltrialkyltin

with

with

organic

analog,

behavior

The radical

anion

radical

AND have

anion

BORIC been

species

of the boron of metallic

is formed

ACID

has

duroquinone,

of the two

In the presence

COMPOUNDS

Allylbisoxyboranes

Interaction

of its

of FB(-CCH3=CCH3-)2BF

which

was

COMPLEXES

obtained

by reacting

Z-chloro-x93,2-dioxaborolane

(40).

of trans-2-chlorobuta-1,3-dienylmercury

chloride

BCl

and subsequent methanolysis yields the compound 3 (67). The same material can trans-CH2=CH=CCl-CH-B(OCH3)2

be obtained and

by interaction

subsequent

a mixture borane

methanolysis;

of cis and trans

also

adds

with

oxyboranesp

however, isomer

carbonyl

been

amines,

latter

is obtained.

as methanolysis

compounds,

vinylacetylene

in this

R2C0,

R,C=CH-B(-0-C(CH3),-)2,

case

Trichloro-

to yield

the

product.

Deproton-

yields

an anion

to form

or with

alpha-trimethylsilylalkylbisoxyboranes Various

have

with

of (CH3)3SiCH2B(-O-C(CH3)2-)2

reacts

form

3

to isopropenylacetylene

CH2=CCH3-CCl=CH-B(OCH3)2 ation

of BCl

species

which

alkenebis-

alkyl

halides

to

(80).

1,3,2-azaoxaboracyclopentanes

obtained

by the interaction

R3Si-NR-CH2-CH2-0-SiR3,

with

of disilylated haloboranes

(861..

ethanol-

209

Characteristic those

physical

N-methylated

data

of the various

derivatives

where

the boron

Closeley

is H, F, Cl or Br are reported.

species

including

substituent

related

is the

species

cl?-/ N\B

I

C6HS

which

was

obtained

phenylborane

with

condensations

from

the reaction

L-2-pyrrolidinylmethanol

occur

on reaction

2-amino-3-hydroxypyridine Bis(divinylbory1) prepared

by controlled The NNR

(249).

terms

spectra

of mesomeric

orbital

of boron

oxides

Reaction molar

of the

and free system

boranes

yields

species

of dioxyborylethyl in carbohydrate 'of complexation been 3

studied

agent

with

moieties,

simple

as well

and_

synthesis

of peptides

di- and

tripeptides. in 381

tris(aminoalkyloxy)-

(261).

For

the employment

as protective

(269, 270).

see

ptY

resolved

tris(ethoxy)borane

0 BC H 2 25'

C6HSB(OH)2

on oxygen

in

moieties.

of organyldihydroxyboranes

using

interpreted

has been in the

into

has been

the vacant

pairs

of the vinyl

liquids

syntheses,

are

between

the corresponding

as distillable

with

of (divinyl)chloroborane

electron

incorporated

of alkanolamines

ratio

borane

((CH2=CH)2B)20,

hydrolysis

to be a useful

it was

analogous

and 2-(o-aminophenyl)benzimidazole.

p-Dihydroxyborylphenylalanine

(237):

(131);

of the cited

interactions

as the pi-electron

was found

of bis(dimethylamino)-

as model

groups

The pH dependency with

compound

diols

has

(266).

3-Aryl-4-phenyl-lp3s5,2-oxadiazaboroles

with

X = OR, C6Hsp

OSiR3,

OSnR3

have

been

synthesized

from

210

N-arylbenzamidoximes The

diborane(4)

derivatives

synthesis

described esters

described

and were

used

of tetraalkyldiboranes(4)

(1,2).

have

via an ate chloride

compounds

bis(ethylenedioxybory1)

methide

(27). Similarly,

complex

which

ion to form esters

species

of the type

(255). utility

to form with

homologation

specres.

Direct

of pinanediol

chiral

have

been

react

rapidly

containing

trigonal

shifts

boron

B-O(pp)pi-interaction

(254);

organylborane boron

derivatives

and for metatheses

of medium

R2BOR

note

-

on the exchange

species 160).

B(OR)3

see

(156).

in the synthesis

ring

size,

Various

series

in terms

(R~B)~~ C2H5).

B(C2H5)2

B-alkenyloxyboroxines

is

in poly-

of.oxyborylated see

studied; vioinal have

order

(-BR-o-)~

(158 to

phenylboronates

acyclic

of

For- a brief

carbohydrates,

(228) has been with

-

groups

For the utiliz&tion

of carbohydrate

of (-BC6H5-O-)s

compounds

in the pi-bond

(R = CH3.

of pure

(227) and acetone

interaction (229).

in the

of O-bonded

The interaction

methanol

can be interpreted

data -

RB(OR)2

hydroxyalkanes.

of boron-oxygen

(6). A decrease

by the 170

indicated

see

rearranges

(252). The l7 0 chemical

-

LiCHC12

to be of general

employing

of 2-ethyl-1,3,2-dioxyboracycloalkanes see

of

of R-CHC1-B(-O-CH2-)2

appears

described

with

which

of alpha-chloro

syntheses

proceeds

ethylenedioxyboryl

the formation

for the preparation

of boronic

alpha-trimethylsilyl-

an intermediate

process

been

the displacement

(30). Cyclic

RB(-0-CH2-)2

temperature

This

yield

has now

lithium

with

the homologous

in high

at low temperatures room

rearranges

for

to aldehydes

interaction

(trimethylsilyl)chloromethyl

boronic

near

been

of carbonyl

in detail

with

(161). and

The homologation via lithium

reaction

B2(t-C4H9)2(0CH3)2

B2(t-C4Hg)3(OCHg) the

in a condensation

with

for the

pentaols,

been

obtained

211

from

the reaction

acid

at 100 to 120°C

in a reverse 0-Borylated

of tris(alkenyloxy)boranes

reaction

the

reduced

to yield

decompose

pressure. are reduced

C6H5CHR-NCH3-BRS

and

(135).

N,N-diorganyl reaction

acetamides

to yield

react

with

alpha-trimethylsilyl-

in a condensation/elimination

heterocyclic

species

of the following

(163):

However,

if R = C6H5

and R" = NR20

containing

trigonal

react

N-trimethylsilylated

with

heterocycles

of substituted

has been

studied

derivatives

mercapto

azomethine

N.N-Diorganyl

monoaminoboranes

substituent

chelates

by spectroscopic

structures

species acetamides to yield

(163)*

diphenylboron

azomethines

the linear

is formed.

of the amine

aldehyde

electronic

boron

of the type

The influence

boron

under

boric

partially

C6H5CHR-NCH3-OBRH,

(Diorganyl)haloboranes

type

species

on heating

hydroxylamines,

by triorganylboranes R"OBR;

(233);

with

of aromatic species

derived

means

and conformations

R in a series

been

salicyl-

(195). Also,

the

of some diphenyl-

and heterocyclic

have

from

studied

hydroxy

and

by electronic

212 absorption

and emission

The data

(219).

intramolecular

spectroscopy

indicate

diphenylboron

Triphenylformaxane, with

diboron

besides

to yield

similarly.

of boron

see

by on

(196).

(R = CeH5),

the

borate

moments

some studies

RRN-N=CR-N=NR

tetraacetate

behave

For

chelates,

tetraphenyltetrazolium

formazanes

dipole

four-coordination

compl.ex formation.

dioximatonickel

and

reacts

species

(164);

other

For the molecular

triaryl-

structure

of diphenylboron-N-methyl-2-oxy-I-naphthaldiminate, Reaction functional chelated

bidentate

with

oximes

such as furfuralaldoxime

of the general

yields

(203):

II /B=.x/C, bidentate

(OH, NH21

of the type

chelate

reagents

in ortho-position oxide

containing

labile

to the azo group

(or trihaloboranes)

to yield

react chelates

(72)x

Reaction

of tris(isopropyloxy)borane,

N-hydroxyalkyl-benzylideneamines or B(sb)3,

sotichiometry The

type

mono-

0

diphenylboryl

ROB(sb)2,

with

(Ill).

O, I”---N

Similarly, protons

of Z-alkoxy-X93,2-benxodioxaborole

structures

a

see

mass

(= sbH) give

respectively,

of the reagents spectral

B(OR13,

depending

with

(RO)iBsb, on the

(65).

fragmentation

of dioxazeboracyclo_

213

alkanes

and

existence between mass

(aminoalkoxy)diphenylboranes

of intramolecular N and

B when

spectral

aromatic

Boron bases

steric

compounds

complexes

(175) and

acetophenone synthesis

and

hindrance

of SCHIFF

bases

of bifunctional

tridentate

to yield base

LB-0-B(OAc)2

solutions

tridentate

(71j. SCHIFF o-hydroxy-

described.

aldimines,

((Ac0)2B)20,

For

the

see

reacts

(173).

with

in lrl and I:2 molar

(LB)20

Complex acid

(where

ratio

IX2 = SCHIFF

acid

of aqueous

complexes

see

equilibria have

been

of boric

acid

and polar

can be extracted

+ H20.

with

(ROBS)-

glucose-borate metric

slowest

Association

been

tiete&c~%~.230

:

and

-.

with

of

organic

the

compounds

(97).

chemistry

of boron

(99).

in organic

solvents

and in

appears

to proceed

have

The

#

to involve

been

determined spectral

syntheses

in stepwise the

(Ro(Ho)~B~B(~R)(oH))-

for the mannitol-borate

some infrared

(206).

solution

(96) as were

step is likely

constants

reported

acid

have

2,6-dimethyl-4,6-octanediol

+ RoB(~fi)~

complexes

titration

acids

with- 2-methyl-2,4-pentanediol

The hydrolysis of B(OCH3)3 ! 3 [the presence of metal alkoxides

Iequilibrium

of boric

studied

in the analytical

(73); the

salicylic

in aqueous

and glycol

can be applied

and methanol

(244).

(98), and the extraction

[fashion

with

For the reactions

formation

interactions Boric

acid

(243).

alcohols,

boric

conductivity

of boric

studied

oligo

have

of

of oxybis(diacetoxyborane)

bases

and

chelates

from

been

The

(207). The electric

been

SCHIFF

(119).

tridentate

derived

(176) have

characterization

boron studied

of bifunctional

Oxybis(diacetoxyborane?, dibasic

been

the

interaction

is absent

of various

has also

and amines

derivatives

donor-acceptor

fragmentation

azo

indicates

and

by potentiodata

on such

species

and derivatographic

214

as well

as infrared

of diols

spectroscopic

and polyalcohols

extraction

of boric

diol have

been

acid

acid with

X-ray

crystallographic

citric

reported

where

see

have

been

also

167).

considered NMR

/

r-7

2

2%

formed

see

metal

by

(56). An

borodicitrates

bis(p-aminosalicylato)-

(201) have

salicylic

acid

been are

decomposition

studied

described

and else-

of disalicyl-

(206).

DERIVATIVES

boron-substituted

by several

This new

class

data,

ring

systems

I

I

JB-“\5 \

/

P-7 \ f r-7

s\B/s I

1,3,2-dithiaboroles

different

of heterocyclic

as a 5 H-electron

spectroscopic

\

s\

with

obtained

The new

and l,+propan-

ions,

of alkali

complexes

(197) and the

complexes

of rubidium

For the thermal

BORON-SULFUR Various

For

and metal

study

structure

of boron

(202).

borates,

7

acid

reported

2,2-dipropyl-

(199).

(200) and its hydrate

complexes

been

on borate

(100).

The crystal borate

with

investigated

boric

has been

have

studies

system,

routes

(182,

system

see

can be

as is evidenced

by

215

have

also

been

characterized Reaction boranes

and

in detail

(7).

+

RN(BR;)-SSCH~

involves

reaction

depends

of neighboring

on steric

groups;

involving

reaction

factors

this

too RN=S=O

+ (R;B)~o;

of the N=S bond

redox

+ 3

the

into

the B-S

(85). The course

as well

of the

as the reactivity

is illustrated

N,N'-disulfinyl

were

(methylthio)organyl-

according

+ CH~SSCH~

an-insertion

and a complex

derivatives

with

quantitatively

sequence

studies

several

of N-sulfinylamines

proceeds

R;BSCH3 process

obtained

by additional

diamines

and N-sulfinyl

sulfonamides. Systems C2Hs

exist

of the type

(RS)nB(N(CH3)2)3_n

in equilibrium

mixtures

the unsymmetrical

compounds

by NMR techniques

(87); however,

be isolated.

Carbon-13

for C6H5B(SC2H5)2 The crystal heterocycles -SBNNB-,

containing

essentially

coplanar.

BORON-NITROGEN

been

dimethylbokes

of

cannot

been

reported

(87). of the permethylated

arrangements

atoms

in both

-NBSSB-

and

by X-ray systems

are

di- and trisilylamines

one Si-H.bond

conditions,

be obtained

employed

data have

determined

the

(52); however,

(R2SiC1)2N-BH2

and

(R2SiCl)(R)N-BHCl

and were- characterized

to prepare of *he

a variety

type

depending

silylaminoboranes

(M-Iiithiomethylau&no)dimethylborane, been

species

structures

chlorinates

(R3Si)(R2SiCl)N-BHCl, can also

the presence

COMF'OUNDS

at least

on the reaction

have

the annular

Trichloroborane containing

shift

the annular

respectively,

R = CH3 or

n = 1 or 2 can be demonstrated

(CgH5)2BSC2Hg

and molecular

(250):

in which

the pure

chemical

and

diffraction

8

with

with

(R = CH3).

Li(CH3)N-B(CH3)2,

has

of N-functional-(amino)-

X(CH3)N:B(CH3)2

with

X =

216

sCH3-N(CH3)2, As(CH3)2

(8). HgCH3

The first trigonal

to electronic

and & Hg

monomeric

boron

effects,

diazaboracyclohexane

(9).

pyrazol-l-ylborane

has been

P(CH3)2,

Si(CH3)2-NCH3-Si(CH3)2Br,

$ Si(CH3)2.

prepared

(112);

containing

it appears

that

due

.

1~3-dimethyl-2-(pyrazol-1'-yl)-l~3~2does not

form a dimeric

pyrazabole

structure.

c”3 ;B-N,O

N

E

Vibrational existence boranes like

spectroscopic

of a linear of the type

arrangement

does not

hand,

makes

this

the rigid compound

good

agreement.

involving

a trigonal-planar

maintained

groups,

imino-

this

allene-

strength.

On the

in (CF3-)2C=N-B(N(CH3)2)2

of the

of angle

species

strain

tricyclic

and experimental are

in

on hybridization

trisaminoboranes

structure

number

increasingly

the

of the compounds

and theoretical

on the four

ethylene

increasing

moiety

unit

structure

The effect

studied

of the general

C=N-RR2

support

However,

the N-B bond

colored

on the electronic

data

in monomeric

(187).

of the central

data

has been

skeleton

R2C=N-BR;

seem to enhance

other

pyramidal

C=N-B

and NMR

and/or

trimethylene

of ethylene

versus

bridges

trimethylene

.array of the dentral

distortetd

but a semblence

by rehybridization geometry:In

the molecule

BN

3

bridges,

moiety

is.

-of coplanarity

of the nitrogen.atoms

the -case of.all exists

(152). With

as a dimer

bridges involving

is

into _

being

ethylene

f&r._

217

coordinate normally

boron. also

gas phase

The bisethylene-bridged

as the

at high

dimer

have

the monomer

spectra

been

of the fundamentals

A new

of several

recorded

are

in the

bis(dimethylamino)-

and the proposed

substantiated

diborane(4)

(1)

(N(CH3)2)2

derivative

assignments

by a normal

coordinate

synthesis

are

with

amine

(38).

species

intermediates

of 2-aminobenzhydrols

hydes

is the

from

in a one-step

anilines

the aid of (dichloro)phenylborane

The reaction

[derivatives

respectively,

of dimethylamine

organoboron-nitrogen have

and triethyl-

to yield

derivatives

been

with

L-Z-pyrrolidinylmethanol

2-(o-aminophenyl)benzimidazole, ,the elimination

and benzalde-

of bis(dimethylamino)phenylborane

Z-amino-3-hydroxypyridine,

iTechniques

B2(-t-CLcH9)2-

l

(Amino)haloboranes

developed

in all

and

proceeds

with

heterocyclic

cases

(131).

for the preparation

of

of triazadiborolidines

one boron

b MFt spectroscopic [reported.

prevails

(162).

treatment

iin which

exists

temperatures.

The vibrational haloboranes

but

species

atom data

The crystal

is replaced of these

novel

and molecular

$.2,4,3,5-triazadiborolidines

by Si, P or As

have

ring

systems

structures been

studied

Idiffraction (250). The 1,2,5-azadiborolene

(91); are

of two by X+ray

is obtained

from

S-containing (R = CH3)

the reaction

organoboron

(142).

The

heterocycle

compound,

metal .carbonyls to form (C5Hs)CoL LCoLCoL

X = S, NR,

with

species

Reacting

complex

X(SiR3)2

(R = CH3,

(R'

= H.

yields

CH3)

the heterocyclic

(167)~

\

CiB

f-L \

1

N-N

“Bh/Bc’

.CHJ

CH;’

Most

transition

with

such as LFe(C0)3,

respectively,

RC=CR /

(R3Sn)2NR

C12B-CR'=CR'-BC12

C12B-CH2-CH2-BC120

and

reacts

complexes

prepared.

NR-NR)

L,

with

the triple-decker

and L2Ni;

was also

of the corresponding

of

the former

tetramethyltin. interacts

can be B-alkylated

The dilithio

with

CH BBr2 3

by reaction

with

salt LiCH=CH-CH,-N(t-C4H9)Li

to form

the following

heterocycle

(218)~

47

B/N-C4Hs I

The latter

species

(LFe(C01212= with

The Fe-Fe

500 to 600°C the

bond

of gaseous

yields

nature

obtained.

and the B-N 2045

cm-',

steric lead

Fe(CO)5

of this

to give

complex

the dimer

can be oxidized

of R and

In

R'

stretching

In

the

case

as well

the monomer

mode

the compound

to the formation

(5).

monomer

solution

requirements

) species at 33 with n = 1, 2 or 3 depending

RClB-NR'-Si(CH

(-BR-NR*-)n

R* = t-ti4H9, the elusive was

with

12. Thermolysis

on

reacts

in the case

R = C6F5

as the cyclic

is relatively

of the species

reacts

of

as a typical

and dimer

stable

is assigned dienophile.

at The

of R = C F and R' = mesityl 65 of the following species:

219

CH3

,B-NH

The role

of iodine

dimesitylboranes

in the photocyclization

has been

concentration-dependent

and was found

substituted

borazine

R = CH

has been characterized 3 of the B-N and C-C stretching modes

the infrared

spectra

charged

skeleton

ions

(10).

ing phosphaborazines

.yields

coupling

deduced

see (151).

exhibit are

Mass

strong

coplanar

silaborazines

(CH3)2Si(NCH3Li)2

peaks

with

have

the

been

and CH3BrB-NCH3-

be converted

in turn,

(10).

of substituted

borazines

if the rings

from

to the correspond-

(92).

of (CH3)2S(=NSiR3)2

(R = CH3) with

C6H5BC12

the heterocycle

the crystal Reaction

structure

of C6H$K!_2

a polymer

receered

References p_ 230

of which with

carbonamide

considerable

was

determined

02S(NR-SiR3)2

of the composition

N-Borylated have

has been

fields,

Permethylated

/ obtained, e.g., from / jSi(CH3)2Br, and may.

Reaction

(8). A distinct

spectra

force

of phenylated

for doubly B3N3

of the

by UREY-BRADLEY

spectra

R3B3N3R2(SiR3)

of B-perdeuterophenylborazines

For the interpretation borazines

to be

(215) .,

The unsymmetrically with

studied

of (anilino)-

(105).

(R = CH3)

gives

02S(NR)2BC6HS. derivatives attention.

and related

For example,

species

220

N-trimethylsilylated react

with

species

ureas

(diorganyl)haloboranes

with

the elimination

An analogous

reaction

thioureas

(63).

migration

is observed

coordinate

to give

in

However,

some

to yield which

with

(186).

the corresponding

instances

boryl

group

isothioureidoboranes.

may feature

intramolecular

bonding.

Condensation

of carbohydrazide

bis(dimethylam%no)phenylborane, BN,+C ring

the N-borylated

of trimethylhalosil.ane

is observed

RR'N-C(=NR)-NR**-BR'", N-B

of the type RR'N-C(0)-NR"-Si(CHg)3

system

with

borane(3)

respectively,

or

leads

to a

(68):

i?

HN’ ‘NH i I HN\B/NH R A series

of linear

N,N'-bis(boryl)hydrazines

of the type

CH3XB-NCH3-NCH3-BXCH3

(X = F, Cl. Br. SCH3.

has been

spectroscopic

prepared

are reported A wide has been data

and

on the

CH3)

species

(62). variety

and

species

oxide

of the reactants

some

characteristic

are reported

The 1,3-addition the aldimine

process

-NR1-BR2R3 f

spectroscopic

(113).

C6H5CH=N(CH3)0

with

2

of (dimethylamino)dichloroborane leads

the following

Z-Pyridylaminoboranes exothermic

RSO

of sulfonamidoboranes,

synthesized

on the

data

N(CH3)2,

according

react

to an equilibrium

heterocycle

with

to (263):

to

(135)x

carbodiimides ..

in an

._ -

221

+

C(=NR’J2

-

@R2

H

The resulting

species

HCl.

of trialkylboranes

Reaction

yields

are readily

iminodialkylboranes

protonated with

with

ethereal

N-alkylbenzamidines

of the type

&N-BR; CGH5 - C ‘NHR

which with

tend

to dimerize

carbodiimides,

(264).

Reaction

of these

C(=NR2) BP produces

species

heterocyclic

compounds:

R2$

N, _.--a -_

R2N,Q;~~ RARl

9

IZWIS

ACID-BASE

Borane bases

adducts

the anular donor

RELATED

MATERIALS

of heterocyclic

and aminopyridines

of the base

nitrogen

atom

with

have

dimethyl

was always

nitrogen been

obtained

sulfide-borane

found

to serve

(53):

as the

site. Primary

and

secondary

stereoselective

in protic are

AND

of a variety

such as chinoline

by interaction

and

ADDUCTS

borate.

from

polyetherslto References p_ 230

of diborane(6)

.

patterns tetradyro-

been

acetophenone

observed

with

a

(37):

reacts

-form LEWIS

or sodium has also

efficient and ketones

(36); the reactivity

of- benzaldehydeand

not B2H6

are mild,

for aldehydes

stereoselectivity

of amine-boranes

BF3.but

agents

solvents

those

A remarkable

in the reduction .variety

reducing

or aprotic

different

amine-boranes

with

acid-base

acyclic adducts

and

cyclic

(137).

-(crown)

On the basis

':.

. .

222

of thermochemical decrease

in

data

it was

the series

BX

3

shown

- BR

3

that

- R2BOR

the acceptor - RB(OR)2

powers

- B(OR)3

(118). Triethylenediamine ether

as TED(BF3)2

(TED) precipitates

and as TED-BFg

tetramethylethylenediamine from

either

solvent

2-Ealogenated and

BBr

except

3'

from

(TMED)

form

in the case

tetrahydrofuran,

1~1 molar

case,

BH

3

adducts between

with BBr

BH

3

(204);

reaction

bromo-(2-pyridyl)methylideneamino-dibromoborane,

an insertion

C5H4N-2-(CBr=N-BBr2).

Dimethylsulfide-trihaloboranes

reportedly

reagents

convenient

Triarylboranes (117):

form

a correlation

the nature

nucleus with

for the dealkylation

and position

acetamide

forms

of WY1

to give

with

the chemical

of substituents

hydrazines stability

on the aromatic

1,3-Diphenylguanidine

lrl molar

to the imino a 1x1 molar

complexes

complexes

group

(165).

complex

with

reacts

in which

the

And N,N-dimethyl (dimethyl)bromo-

(163).

Tertiary

aminecomplexes

L-B(ON02)3

have

compounds

(120).

been

recorded

spectrum

and was analyzed

of (CH 0) P-BH

have been (CH&As-BX3

33

examined

structures

3

as stable,

(57). Also,

and deuterated

suggested

of trimethylamine

crystalline

the vibrational

(205).

complexes

has

the vibrational

derivatives

Br, I) are reported

are

of the type

of acetonitrile-borane

(84). Elsewhere,

(X = Cl,

to the fundamentals

of trinitratoborane

synthesized

The vibrational

spectra

between

of the triarylboranes.

is bonded

borane

1x1 molar

exists

triarylboranes

boron

been

are

(191).

ethers

and

3

and

2-cyanopyridine yields

latter

whereas

(49).

adducts

of the reaction

in this

diethyl

and TED precipitates

as the 1x2 molar pyridines

BF3 from

and

thereof spectra

assignments

The molecular

of BC13 and BBr3

of

223 have

been

determined

by gas-phase

H3N-BH2COOH.

Ammonia-carboxyborane. of glycine,

has been

evidence

a dimeric

boranes,

R3%'CHR'zH3

ylids

with

structure Species

prepared

and X-ray

structure , have

THF-borane

(208).

been

been prepared

by reaction

phosphine

with

based

BH3 group

is bonded

THF.BH3;

(259).

bicyclic

aminophosphanes

Bisborane

position

adducts in which

and bonded

(253).

Crystal

bonded

to P and N, evidencing

character

10

structure

Bonzoate give

AND

' Divalent a pyridine

the P atom

that

the

the pyridyl by certain

is in a two 0 atoms

the borane strong

NMR

in CDC13 spectra

cations

is

basic

or CH2C12

which

indicate

(4); for the cation

(where

bromine

derivatives).

L3BH2+

I- or pF6-)

factors

iodine

(where

have

on (CH3)3N-BHBr2

(70). The displacement

and also

halogen

of the type

are Br-.

displacement

steric

amine

than

can be formed

solutions

cations

pyridine-dihaloboranes

attacking

rather

data

SPECIES

fluorine-19

and anions

by favorable

with n = 1

(147).

boron

by nucleophilic

(108).

of the respective

an unusually

of (ester)2BF2+ see

of

and molecular

determined

confirm

BORATE(l-)

low-temperature

(hmpa)2BF2+,

by reaction

atom.

ester/BF@Clg

the existence

data

to one N and

data

of the latter

BORONIUM(l+)

diffraction

on spectroscopic

to the P atom

nitrogen

bridgehead

analog

(C6H5)3_n(2-C5H4N)nP'BH3

to 3 have

(134).

the boron

obtained

has been

diffraction

Some phosphanealkylene-

The crystal

(83).

of (CH~)~%CH~"H~ of the type

electron

derivatives

react

cbtained

or is controlled

in and the basicity

by the nature

been

L is

of the

of the displaced faster

than

the

224 The reaction a general lithium

and

of trialkylboranes

convenient

trialkylhydroborates

trialkylhydroborate has been (18).

illustrated

(41).

been

The role agent

by a series

has also

found

presence

a

mild

of transition

metal

of lithium

in organic

to exhibit

of alkyl

desulfurization

syntheses examples

exceptional

halides

of thiols

chlorides)

is

of

of representative

for the hydrodehalogenation

it effects

t-butyllithium

for the preparation

as a reducing

The reagent

ability and

method

with

(25).

(in the

to yield

hydrocarbons

(129). Lithium vinyl

ketone

reaction with

1-alkynyltrialkylborates

interact

in the presence

in a MICHAEL-tme

(44). Copper(I)

allylic

bromides

The reaction been and

developed sodium

or Z-propinyl

for a new

conjugated

The coupling

dienes

solution

importance

(192).

and the CB bond

atoms

borates,

see

conductances

react

C and been

has

rapidly

(74): with

to afford

several

determined

Examination

others

in

in 1,2-dimeth-

of the 13C NMR

clearly

spectra

the relative

between

the CC double

of the monoetherate consists

of a very

spectra

of tetrameric

of alternating

distorted

cube

Na and H

(236).

of some volatile

metal

tetrabutylborate

has been

For

tetrahydro-

(251).

Tetrabutylammonium as a reference

iodine

(143).

trimethylhydroborate

the vibrational

with

(21).

conjugation

structure

at the corners

couple

of l,l-dialkylethenes

indicates

of sigma-pi

The crystal

have

methyl

(170).

intermediates

q-13

constant

of trialkylallylborates

sodium

synthesis

tetramethylborate

oxyethane

bromide

of vinyltrialkylborates

via alkenylcopper

symmetrical

bond

l-alkenyltrimethylborates

methoxyalkenyldialkylborates

CuBr=(CH3)RS

lithium

of TiC14

with

electrolyte in nonaqueous

for the evaluation solvents

(17).

employed

of single-ion

225

The reaction ratio was

yields,

of (CH3)3SnCF3

BF3 in 321 molar

with

besides

F BCF -, the anion 3 3 as its potassium and cesium

isolated

F2B(CF3)2-,

salt,

(12). The crystal structure of CS(F~B(CF~)~) determined

by-X-ray

of the

species

H3BSiF

- and

3 Reaction

has also

been

H2B(SiF3)2-

of LiSi(CH3)3

formation

studied

have

with

and

Several been

B(SiR3)4-

also

ation

vibrational ammonium gives

potassium

by X-ray

and iodide pairing

but agrees

in solutions

The

detected alkali

salt

first

metal

to proceed

at an iron

or V electrodes, Fluorine-19 have

been

Referencesp. 230

with

from

that

sodium

yields

the

with

crystal

(136).

those

structure

of nitroso (154);

diffraction)

has been geometry

observed

M+(RN(O-)BH3)-,

of

crystal determined

of acetyl-

in the bromide For

tetraphenylborate.

ion.

see

have

compounds

(239).

been

with

the reaction

is likely

BH3*-.

cyanotrihydroborate

in acetonitrile

(CH3CN)qPe(BH3CNf2;

but at MO

the salt is oxidized

determined

phenyl-

In conjunction

of the chloride.

anion

of sodium

chemical

-,

evaluated

the direct

the molecular

differs

the radical

electrode

been

tetraphenylborate

the reaction

Electrolysis

3

of the

The

tetrahydroborates

via

properties

bonding

boronitroxides,

during

RjBSiR

by X-ray

(101);

of

to the

(as determined

of acetylcholine

in this

leads

tetraphenylb_orates

effects

studies,

of hydrogen

diffraction

(81).

such as

ion have

(223).

tetraphenylborate

structure

choline

species

spectroscopic

anions

(14).

tetraphenylborate

evidence

boranes

(95) and the reagent

of tellurium

spectrum

The related

reported

anions

tetrakis(3,5-dichlorophenyl)borate (94). Sodium

has been

(114).

been

various

ring-substituted

prepared

respectively

and the vibrational

of trimethylsilylborate

RiB(SiR3)8-

have

diffraction

which

shifts

to Na(H3BCNBH2CN)

(213).

in some tetrafluoroborates

(79). A molecular

orbital

study

on XBH

3

-

species

(X = Li,

reported

BeH,

elsewhere

BH,, CH3,

(61).

Dihydroxyboranes, or OH, form agents

and were become

found

more

complexes acid,

leads

11

METAL

treatment

to the formation

C6H&-3-NO2

chelating

mannitol

or

RB(OH)L-

_5

complexes

f H30*

were

and boron

of a mixture

determined

acid of biuret

of bis(biureto)boric

the K, Cs. Tl and Ag

salt

of which

(3).

DERIVATIVES

(Chloro)divinylborane BC13 and

acid,

as the ligand

Thermal

C6H5,

bidentate

salicylic

of such

H(B(-NHCONHCONH-)2).

described

with

constants

acidic.

are

R = CH3,

+ H2L

to increase

acid

with

to: RB(OH)2

stability

boric

acid,

111 molar

according

(46). The

with

RB(OH)2

such as-oxalic

catechol

OH and F) has been

NH2,

can be generated

(CH3)2Sn(CH=CH2)2

photochemical displacement

conditions

(39); with

of two CO groups

in situ from

the species

reacts

Fe(CO)S

or C5H5Co(C0)2

to form

complexes

under by

of the type

2

B-Cl

M

with

M = Fe!CO)3

halogen complexes

can be replaced

H ). respectively. 55 to give additional

The boron-bonded vinylborane

of the same type.

The complex and its structure Complexes

or Co(C

(CH3B(-CH=CH-)2BCH3)Co(C5H5) was

determined

of the divinylborane

and L = X(-CH=CH-)2BC6H5 been prepared

(221);

have a sandwich-type C2 molecular

by X-ray

diffraction

type ML2 with

(X = G(CH3)2,

based

has been

on NMR

data,

bis(q 5-divinylborane)meta1

symmetry.

(115).

M = Pd, I%, Ni

Si(CH3)2.

spectral

synthesized

(CH2)2)

have

the compounds structure

With

227

Reaction species

of Co(C5H5BCH3)2

(CO>_,Mn(CSHSBCH3)

the latter

compound

with

in a ligand

can be acylated

borinato)tricarbonylmanganese. sandwich

complexes

SB2C2-Fe-C5HS

- (157);

respectively,

or CoC12, diffraction

data

with

The Fe-Fe

and the process whereas

formation

under

results with

whose

(C5H5Cr(N0)2)2

formation

metallic

reaction

yields,

NO groups

species

anion

with

FeC12

complex.

X-Ray

are given.

of (LFe(C0)2)2 can be cleaved

(107). with

iodine

of LFe(CO)21; gives

(CH3)_jSiC1 results

among

triethylhydroborate other

this

result

in the

Various

studies

complexes

derivatives

are

of iron(I1)

rhodium

(179).

alsothallium(II1) Triha+oboranes

by a X-ray

(47),

tungsten

with

metals? iridium

triethylborane SWuCture

polypyrazol-l-ylthese

(179),

(220),titanium

(103). form

the species

(257).

concerned

of transition

with

one of the original

by a bridging

is confirmed species

products,

in which

is displaced

qf the

(104).

reacts

potassium

with

of lithium

determination

borate

the

sandwich

in the formation

.(CgH5)2Cr2(N0)3(CzH5B(C2115)2).

.moietyt

from

of LFe(C0)2Si(CH3)3.

The reaction

bridging

the

species

of tetradecker

type CSHS-Fe-SB2C2-M-

the cited

of the compound

reduction

K(LFe(CO)2),

to give

(214):

(= L)

Fe(C0)5

linkage

gives

reaction

synthesis

the latter

for the Fe

The azaboroline

reacts

A new

which

the

to (2-acetyl-l-methyl-

M = Fe or Co originates

((C5HS)Fe(C2B2S)2)2Zn.

yields

transfer

of the generalized

with

((C5H5)Fe(G2B2S))

Mn2(CO)10

include palladium(I1) (260).

and

: addJcts

with

(C5H5)Pe(CO)2(COCHa)

228 in

which

This

the boron

feature

ketonate

with

is bonded

is not

surprising,

complexes

of boron

M, for example,

reaction

with

oxygen

since various

metal-

Re(CO)&'

have been with

obtained

trigonal

to form

Br, I and R = CH3

P

-di-

neutral

by the

haloboranes

triacetyltricarbonylrhenate

trihaloboranes

(88).

of the type

of the diketonates

Similarly.

138).

to the acetyl

(9,

dianion

compounds

where

reacts

X = F, Cl.

(178)~

CR-O \

/ (OC~3R~-CR-O--BX \

If

/

CR-O

X =

(178);

Br,

the

halogen

is

and

the

crystal

structure

has been

determined

readily

by X-ray

displaced of

the

diffraction

by

alkoxy

species

with

which

was

with 4,4'-dipyridine, determined

tetraphenylborate described In Mn atoms Ag(I)

as

bridged

Several

structure.

H(BH4)(P(CH3)3)4Mo

BH4

For the

synthesis

, see

a singly and

have

link

been

the two complexes

units

structure

has been

have

of been

hydrogen-boron-

(77). The crystal.structure

(CO),(CH3)Fe(P(CH3)3)2(CNB(C6H5)3)

of

(43).

or H3BC02C2HS

involve

II

complexes

bridges

species

a

(18~))~ Zwitterionic

catalysts

H-B-H

forms

structure

tris(methyldiphosphine)

containing

(51); the

metal

homogeneous

(p-Br)(C0)6(B3H8)Mn2. (177).

the crystal diffraction

- transition

stable

and CutI)

prepared

by X-ray

X = Cl

(139).

Bis(difluoroborondimethylglyoximato)nickel~II) 1x1 adduct

groups

of of

investigated

by

229

X-ray

(166).

diffraction

preparations

Electrochemical

of isomers

of bis(cyanotrihydroborato)tetrakis-

(trialkylphosphite)iron(II)

12

PHYSIOLOGICAL

AND

A voluminous

application medicine

of boron

(188);

summarized

(265).

have

been

prepared,

biological

activity

some

found

another walls

on the

on the and

on plants

species uracils

of which

were

has been

(189).

one has been

analog have

porcine found

been

activity

and related

of compounds

(organyl)hydroxyboranes pancreatic

to bind

thereof

to exhibit

The antiflammatory

Some

of

and analogs

found

amine-carboxyboranes

to inhibit

lipase

reversibly

have

(102),

to cell

(169). Stable

long-term

morphological

treatment

phenylborane ofboron cotton have

pharmacy

of boron

borylated

(145).

amine-cyanoboranes,

been

(76).

reported

references

in biology,

action

studies

Several

described

up-to-date

of the boron-containing

and NMR

described

been

(132).

The biosynthesis

has been

presents

and toxic

have

ASPECTS

compounds

elsewhere

aplasmomycin

complexes

RELATED

book

and metathetical

of Riccia

(13). Another

fibers

reported

inhibiters

in relation

with

(dihydroxy)-

(59) reports

(59). group

it may be noted to doses

of boron

(256).

References p_ 230

observed

of glucose

in vitro as a new

been

after

on the effect

from UDP-glucose

into

(Phenyl)hydroxyboranes of pep-tidy1 transferase

(23S).

Finally,

the effect

grown

have

fluitans

study

on the incorporation

been

studied

changes

that

and forms on plant

boron

of nitrogen

productivity

mobility

in the soil

fertilizers have

been

ano

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