The Journal of Organic Chemistry

A facile preparation of N-(isopropoxyalkyl) amides by generation and trapping of N-acyliminium ions from ionization-rearrangement reactions of N-triflyloxy amides

RV Hoffman, NK Nayyar

Index: Hoffman, Robert V.; Nayyar, Naresh K. Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3530 - 3539

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Citation Number: 26

Abstract

A series of hydroxamic acids were converted toN-triflyloxy amides which were heated in 2- propanol to give N-(1-isopropoxyalkyl) amides in high yields. The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, as well as in the 1- isopropoxyalkyl group. N-Alkylation of secondary N-(1-isopropoxyalkyl) amides can be used for converting them to tertiary N-(1-isopropoxyalkyl) amides. N-Acyliminium ions of wide ...