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A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters

✍ Scribed by Björn C. Söderberg; Shannon N. O'Neil; Angela C. Chisnell; Jian Liu

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 148 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00216-7

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✦ Synopsis

AbstractÐA novel [3.3]sigmatropic rearrangement of in situ formed a,b-unsaturated Fischer acyloxy carbenes forming alkynol esters is described. For example, reaction of tetramethylammonium pentacarbonyl(1-oxo-2-butenyl)chromate(1-) (4) with 4-methoxybenzoyl chloride gave 2-methyl-3-butyn-2-yl 4-methoxybenzoate (8) in 32% yield. In addition to the rearrangement products, dienol esters formed by a formal b-hydride elimination-reductive elimination sequence were usually isolated. In the above example, 3-methylbuta-1,3-dien-1-yl 4-methoxybenzoate (9) was obtained (16%) as the side product.

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