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Cyclic alkenenitriles: chemoselective oxonitrile cyclizations
Journal article   Peer reviewed

Cyclic alkenenitriles: chemoselective oxonitrile cyclizations

Fraser F Fleming, Lee A Funk, Ramazan Altundas and Vaqar Sharief
Journal of organic chemistry, v 67(26), pp 9414-9416
27 Dec 2002
PMID: 12492346

Abstract

Potassium tert-butoxide triggers the chemoselective cyclization between nitrile anions and remote, enolizable carbonyl groups, despite the acidity difference favoring enolate formation and addition to the nitrile group. Domino deprotonation, cyclization, and dehydration efficiently transform a diverse array of omega-oxonitriles into carbocyclic and heterocyclic five- and six-membered alkenenitriles in a single synthetic operation.

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Web of Science research areas
Chemistry, Organic
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