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Reactions of α,β-Enones with Diazo Compounds, Part 3 : On the Nature of the 1,5-Ring Closure of α,β-Enone Ylides

✍ Scribed by Olcay Anaç; Ayşe Daut Özdemir; Özkan Sezer

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
167 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Carbonyl ylides arising from ethyl acetodiazoacetate/dimethyl diazomalonate and α,β‐enones with mainly s‐cis conformations underwent disrotatory cyclization to produce dihydrofuran derivatives. This process proved to be sensitive to steric effects. The corresponding ylides arising from rather s‐trans α,β‐enals yielded dioxole derivatives. The mechanisms of the reactions are discussed.

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