Reactions of primary and secondary amines with fluoronitrene generated from isopropyl N, N-difluorocarbamate

DL Klopotek, BG Hobrock, P Kovacic…

Index: Klopotek, David L.; Hobrock, Brice G.; Kovacic, Peter; Jones, Martin B. Journal of Organic Chemistry, 1980 , vol. 45, # 9 p. 1665 - 1667

Full Text: HTML

Citation Number: 3

Abstract

Isopropyl N, N-difluorocarbamate deaminates primary amines, RNHz, affording RH, Nz, RNHC02-i-C3H7, and RNHz. HF. With secondary amines, dibenzylamine gives bibenzyl, whereas pyrrolidine yields a ring-expansion product, 2, 3, 4, 5-tetrahydropyidazine. The reactions are consistent with the generation of fluoronitrene and subsequent production of the intermediates RN= NH from RNH2 and R2N= N from RzNH. The advantages of using ...