The Journal of Organic Chemistry

Direct conversion of aliphatic carboxamides to alkylammonium tosylates with [hydroxy (tosyloxy) iodo] benzene

IM Lazbin, GF Koser

Index: Lazbin, I. Mark; Koser, Gerald F. Journal of Organic Chemistry, 1986 , vol. 51, # 14 p. 2669 - 2671

Full Text: HTML

Citation Number: 52

Abstract

The utility of [hydroxy (tosyloxy) iodo] benzene (2) as a" Hofmann reagent" has been explored. Treatment of various primary, aliphatic carboxamides (RCONH2, R= methyl, ethyl, isopropyl, tert-butyl, n-pentyl, n-heptyl, undecyl, allyl, benzyl, cyclobutyl, cyclohexyl) with 2 in acetonitrile at reflux gave the corresponding alkylammonium tosylates (RN+ H3-OTs) in yields ranging from 57% to 94%. The alkylammonium tosylates separated directly from the ...