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A novel synthesis of epoxides and allylic alcohols from carbonyl compounds through α, β-epoxy sulfoxides

✍ Scribed by Tsuyoshi Satoh; Youhei Kaneko; Koji Yamakawa

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
203 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of s,8-epoxy sulfoxides, easily prepared from carbonyl compounds with 1 equivalent of n-butyllithium at -100 'C gave the desulfinated epoxides in good yields.

The similar a,8-epoxy sulfoxides having arylmethyl group at a-position, on treatment with excess n-butyllithium at -70 "C afforded 3-aryl allylic alcohols.

📜 SIMILAR VOLUMES

A short synthesis of α-allenic alcohols
A short synthesis of α-allenic alcohols from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide
✍ Tsuyoshi Satoh; Takafumi Noguchi; Toshifumi Miyagawa 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 188 KB

The reaction of the a-sulfinyl carbanion of dichloromethyl p-tolyl sulfoxide with a,b-unsaturated carbonyl compounds gave 1-chlorocyclopropyl p-tolyl sulfoxides having a carbonyl group in good to high yields. The carbonyl groups in the products were reduced or treated with alkylmetals to give alcoho