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Vicinal dianions of diethyl α-aroylsuccinates: a general synthetic route to α-aroyl- and α-arylidene-γ-butyrolactones

✍ Scribed by Manat Pohmakotr; Laddawan Sampaongoen; Arisara Issaree; Patoomratana Tuchinda; Vichai Reutrakul

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 418 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01622-8

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✦ Synopsis

Vicinal dianions derived from diethyl a-aroylsuccinates were found to react with carbonyl compounds b-regioselectively to afford a-aroyl-g-butyrolactones, which were converted into a-arylidene-g-butyrolactones by reduction with H 2 /Pd-C followed by elimination employing methanesulfonyl chloride in pyridine. The method provides a general and convenient route to a-aroyland a-arylidene-g-butyrolactones.

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