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Reaction of Baylis–Hillman products with Swern and Dess–Martin oxidants

✍ Scribed by Nicholas J Lawrence; J.Paul Crump; Alan T McGown; John A Hadfield

Book ID
104230653
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
65 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Baylis-Hillman adducts of aryl aldehydes and alkyl acrylates are efficiently oxidized to the corresponding a-methylene-b-keto esters with the Dess-Martin periodinane. The attempted Swern oxidation of the same adducts resulted in S N 2%-type substitution of the allylic hydroxyl group by chloride.

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