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Acceleration of the Dess-Martin Oxidation by Water

✍ Scribed by Meyer, Stephanie D.; Schreiber, Stuart L.

Book ID
115471275
Publisher
American Chemical Society
Year
1994
Tongue
English
Weight
445 KB
Volume
59
Category
Article
ISSN
0022-3263

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Reaction of Baylis–Hillman products with
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✍ Nicholas J Lawrence; J.Paul Crump; Alan T McGown; John A Hadfield 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 65 KB

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.