Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Oxidative Generation of N-Acyliminium Ions from N-1-(Tributylstannyl)alkyl Carboxamides and Carbamates and Their Reactions with Carbon Nucleophiles
Koichi NarasakaYasushi Kohno
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1993 Volume 66 Issue 11 Pages 3456-3463

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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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© 1993 The Chemical Society of Japan
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