Chemistry of carbonnitrogen multiple bonds. The useful synthon CF2NBr

92

B-9 CHEMISTRY OF CARBON-NITROGEN SYNTHON CF2=NBr D. D. DesMarteau*, Storzer Department

MULTIPLE BONDS. THE USEFUL

B. A. O’Brien, C. W. Bauknight Jr., S. Singh, S. Hwang and W.

of Chemistry,

Improvements

in

Clemson University,

the

synthesis

Clemson, SC (U.S.A.)

of

g-bromo-difluoromethanimine,

CF2=NBr. will be described along with some reaction chemistry. The imine undergoes thermal addition with a variety of olefins, leading to the simple addition product and to the formation of telomers. with CO forms the isocyanate BrCF2tJ=C=0,in high yield. CF2=UBr at

-

450°C gives high

butadiene, CF24WJ=CF2.

yields of

Photolysis

Pyrolysis of

tetrafluoro-2,3-diara-1,3-

making this compound readily available for the

first time. Some new reaction chemistry of the diene will be discussed.