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The acylation of acetylenes with β, γ-unsaturated acid chlorides: a new sysnthesis of 5,5-disubstituted 2-cyclopentenones

✍ Scribed by Martin Karpf

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 251 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85748-2

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✦ Synopsis

Ihe acylatlon of acetylenes mth ol,a-disubstltuted, B,y-unsaturated acid chlorides was found to lead to 5,5-disubstltuted 2-cyclopentenones by a novel intramolecular cycllzatlon-rearrangement process. lhe acylatlon of trimethylsilyl substituted acetylenes Fnth allphatlc and aromatlc acid chlorides, activated by aluminum chloride, generally leads to a-acetylenic ketones by substltutlon of the trlmethylsllyl group.ly2 We have found that this reaction mth 3,y-unsaturated acid chlorides takes a different course, depending on the c+substitutlon of the acid chloride.

Upon addltlon of a mixture of 13 and trlmethylsllylacetylene to aluminum chloride In dichlorcmethane at -70°C, followed by acid hydrolysis after warmlng up to 4 was obtalned4y5, separable by column chromatography.

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