Helvetica Chimica Acta p. 73 - 85 (1984)
Update date:2022-08-16
Topics:
Karpf, Martin
The acylation of acetylenes with α,α-disubstituted, β,γ-unsaturated acid chlorides under Friedel-Crafts-type conditions leads to 5-substituted 2-cyclopentenones.Phenols are formed with β,γ-unsaturated acid chlorides bearing at least one α-H-atom.These transformations are explained by the intramolecular cyclization of the initially formed vinyl cation, which, in the cases of α,α-disubstituted acid chlorides, is formed by ring contraction.The reaction leading to 2-cyclopentenones is applied to the syntesis of some spiro<4.5>deca-2,6-dienones.
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