REACTIONS OF PHENYLCHLORODIAZIRINE WITH NUCLEOPHILES AND SUBSTITUTED ACETYLENES

The chemistry of phenylchlorodiazirine (I) has been investigated with emphasis on the nucleophilic attack on the nitrogen-nitrogen double bond and the formation and chemistry of phenylchlorocarbene. Treatment of I with phenyllithium afforded diphenylbenzamidine, whereas reaction with methyllithium gave acetophenone. The reaction of I with sulfonium and phosphonium ylides was also studied. Like other diazirines, phenylchlorodiazirine decomposes thermally to produce phenylchlorocarbene, which may be trapped with triphenyl-phosphine, tri-n-butyltin hydride, and substituted acetylenes. © 1969, American Chemical Society. All rights reserved.