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Synthesis of perfluorobicyclic ethers
50
o-1 1 SYNTHESIS OF PERFLUOROBICYCLIC
ETHERS
Takashi Abe*, Hajime Baba, Eiji Hayashi and Shunji Nagase Government
Industrial
Research Institute,
Nagoya, Hirate-machi,
Kita-ku, Nagoya 462
(Japan)
The electrochemical fluorination of cycloalkyl-substituted acetic and propionic acids were conducted to obtain several kinds of perfluorobicyclic ethers [reaction conditions: Anodic current density: 3.5 A/dm2, Volt: 5--8V, Temp: 5-6 "Cl. For example, from cyclopentyl-substituted acetic acids, perfluoro(4-alkyl-2-oxabicyclo[3.3.O]octane)s (I) were formed as the cyclization products in yields of 10 -19% toqether with the corresponding perfluoroalkanoyl fluorides (II) (Y=3-13%).
B
E.F.
KOCH3 0 (R=H, CH3, C2H5)
1)
0
0
Pf
F
I
CF$F (II) 0
While, perfluorospiro-ethers were obtained from the fluorination of 3-cycloalkyl-substituted propionic acids. The characterization of these perfluorobicyclic ethers which consists of the reaction with anhydrous aluminum chloride will be reported also.
o-12 ON THE MECHANISM OF ELECTROFLUORINATION G. P. Gambaretto Institute
(*), M. Napoli, A. Scipioni and L. Conte
of Industrial
After
a
Chemistry,
short
review
the electrofluorination veral electrofluorination particular view
attention
to
bring
oxidation radical-cation,
stabllisation
is
new of
of
the
current
their
the
effected
Padua (Italy)
mechanisms,
the
organic compounds carried out for
industrial
mechanism. carried out
lsobutirrlc, bsnzensulfonlc amines ftripropylamine. anodic ming a
via Marzolo, 9,35100,
process of experiments
of the fluorination These experiments
morpholinal,
OF ORGANIC COMPOUNDS
applications
either
with
Authors
are
organic
to
the
mechanism
organic molecule which originates by
addition
suggesting
adsorbed on the the corresponding of
a
fluoride
anion.
HF. with
Ssa
reconsidered
acids
and toluensulfonicl, either trlbutylamine, N-ethylpiperidine support
describe
in enhydrous some years
[butirric.
with and an
tertiary N-methylinitial
anode thus forcation whose
In
o-1 1 SYNTHESIS OF PERFLUOROBICYCLIC
ETHERS
Takashi Abe*, Hajime Baba, Eiji Hayashi and Shunji Nagase Government
Industrial
Research Institute,
Nagoya, Hirate-machi,
Kita-ku, Nagoya 462
(Japan)
The electrochemical fluorination of cycloalkyl-substituted acetic and propionic acids were conducted to obtain several kinds of perfluorobicyclic ethers [reaction conditions: Anodic current density: 3.5 A/dm2, Volt: 5--8V, Temp: 5-6 "Cl. For example, from cyclopentyl-substituted acetic acids, perfluoro(4-alkyl-2-oxabicyclo[3.3.O]octane)s (I) were formed as the cyclization products in yields of 10 -19% toqether with the corresponding perfluoroalkanoyl fluorides (II) (Y=3-13%).
B
E.F.
KOCH3 0 (R=H, CH3, C2H5)
1)
0
0
Pf
F
I
CF$F (II) 0
While, perfluorospiro-ethers were obtained from the fluorination of 3-cycloalkyl-substituted propionic acids. The characterization of these perfluorobicyclic ethers which consists of the reaction with anhydrous aluminum chloride will be reported also.
o-12 ON THE MECHANISM OF ELECTROFLUORINATION G. P. Gambaretto Institute
(*), M. Napoli, A. Scipioni and L. Conte
of Industrial
After
a
Chemistry,
short
review
the electrofluorination veral electrofluorination particular view
attention
to
bring
oxidation radical-cation,
stabllisation
is
new of
of
the
current
their
the
effected
Padua (Italy)
mechanisms,
the
organic compounds carried out for
industrial
mechanism. carried out
lsobutirrlc, bsnzensulfonlc amines ftripropylamine. anodic ming a
via Marzolo, 9,35100,
process of experiments
of the fluorination These experiments
morpholinal,
OF ORGANIC COMPOUNDS
applications
either
with
Authors
are
organic
to
the
mechanism
organic molecule which originates by
addition
suggesting
adsorbed on the the corresponding of
a
fluoride
anion.
HF. with
Ssa
reconsidered
acids
and toluensulfonicl, either trlbutylamine, N-ethylpiperidine support
describe
in enhydrous some years
[butirric.
with and an
tertiary N-methylinitial
anode thus forcation whose
In