✦ LIBER ✦
The Reaction of Cyclopropyl Ketones with Acetyl Methanesulfonate. An efficient ring opening under neutral conditions with regiospecific enol acetate formation and stereo-controlled nucleophilic addition. Preliminary communication
✍ Scribed by Martin Demuth; Palaykotai R. Raghavan
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- German
- Weight
- 181 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Cyclopropyl ketones are readily cleaved under neutral conditions at room temperature by the combined action of acetyl methanesulfonate and nucleophiles such as Br^−^, I^−^, and MsO^−^. The high‐yield reaction involves regiospecific enol acetate formation with a stereoselectivity of nucleophile addition which is compatible with an S~N~2‐type opening of the cyclopropyl ring.