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Synthesis of macrocyclic enaminolactams by ring expansion reaction of 2-oxocyclododecane-1-carbonitrile with diarylcarbodiimides

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
52
Issue
12
Identifiers
DOI: 10.1016/0040-4020(96)00090-7
Keywords
  • Article

Abstract

Abstract A base promoted ring expansion reaction of 2-oxocyclododecane-1-carbonitrile (6) with several diarylcarbodiimides gives 14-membered α-enaminolactams (12–17), whereas N-alkyl-N′-aryl- and N,N′-dialkylcarbodiimides do not react at all. This new process seems to occur by a similar mechanism as some recently reported analogue reactions of heterocumulenes with cycloalkanones. All relevant molecular structures were confirmed by X-ray analysis.

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