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

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 rec...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 12; pp. 4363 - 4376
Main Authors Ivancev, Wladislaw, Ognyanov, Vassil I., Hesse, Manfred
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.03.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONJUGATED CARBODIIMIDES
ENLARGEMENT
IMIDES
DERIVATIVES
CATALYZED CYCLOADDITION
HETEROCUMULENES
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00090-7