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Synlett 1993; 1993(9): 710-712
DOI: 10.1055/s-1993-22582
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Cyanoalkylamines as a Source of Acyclic and Heterocyclic Azomethine Ylides

Robert W. Shaw* , David Lathbury, Timothy Gallagher
  • *Shell Research Limited, Sittingbourne Centre, Sittingbourne, Kent ME9 8AG, England
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Publication Date:
19 March 2002 (online)

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Thermolysis of activated N-cyanoalkyl amines (5) provides access to acyclic azomethine ylides (6). The allenic N-cyanoalkyl amine (10a) undergoes Ag(I)-catalysed cyclisation followed by thermally-induced loss of HCN from (11a) to provide the heterocyclic ylide (12) which has been trapped by N-methyl maleimide.

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