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Reactions of 2-acylbenzoates with dimethyloxosulphonium methylide: A novel route to isocoumarins

✍ Scribed by Kevin Beautement; John M. Clough

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 196 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81355-1

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✦ Synopsis

Treatment of 2-benzoylbenzoates with dimethyloxosulphonium methylide (1) gives 4-phenylisocoumrins (2); methyl 2-acetylbenzoate gives 4-methylene-3,4dihydroisocoumrin

(3) under the same conditions.

Corey's method' for the conversion of ketones into epoxides using sulphonium or oxosulphonium ylides has found widespread use in organic synthesis.

We have now discovered that treatment of 2-benzoylbenzoates with dimethyloxosulphonium methylide (1)

does not lead to epoxides but, instead, directly to 4-phenylisocoumarins (2). We suggest that this takes place via the steps shown in Scheme 1. 2 -

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