Bulletin of the Chemical Society of Japan

Oxidative Generation of N-Acyliminium Ions from N-1-(Tributylstannyl) alkyl Carboxamides and Carbamates and Their Reactions with Carbon Nucleophiles.

K Narasaka, Y Kohno

Index: Narasaka, Koichi; Kohno, Yasushi Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 11 p. 3456 - 3463

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Citation Number: 27

Abstract

Oxidation of N-1-(tributylstannyl) alkyl carboxamides and carbamates with ammonium hexanitratocerate (IV) or ferrocenium hexafluorophosphate generates their N-acyliminium ions by the elimination of tributylstannyl radical under mild reaction conditions. The iminium ions thus formed react with various carbon nucleophiles to give the corresponding addition products.

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