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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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Narasaka et al. (1993) studied this question.
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