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Regioselective Addition of Trimethylsilyl Cyanide to β-Alkoxyvinyl Alkyl Ketones

✍ Scribed by Igor S. Kruchok; Igor I. Gerus; Valery P. Kukhar

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
118 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐThe 1,2-and 1.4-addition reactions of trimethylsilyl cyanide to alkyl vinyl ketones were studied. Regioselectivity of this reaction depends on the structure of alkyl vinyl ketones, the reaction temperature and the nature of catalyst. The presence of alkoxy group in b-position of a,b-enone is the important condition for realization of 1,4-addition. Ambient temperature (258C) or base catalyst (NEt 3 ) directed the reaction predominantly into 1,2-addition; higher temperature, electrophilic catalyst (I 2 ) and bulky alkyl substituents near the carbonyl group directed the reaction in 1,4-addition route. Hydrolysis of 1,4-adducts yields saturated ¯uorine-containing ketones containing CN-and ethoxy groups at the b-position.

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Addition of trimethylsilyl cyanide to α-
Addition of trimethylsilyl cyanide to α-substituted ketones: Catalyst efficiency
✍ W.J. Greenlee; D.G. Hangauer 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 104 KB

Addition of trimethylsilyl cyanide to o-substituted ketones is often slow and incomplete when catalyzed by zinc iodide. Use of potassium cyanide/la-crown-6 complex as catalyst is a superior method, providing high yields of adducts. The addition of trimethylsilyl cyanide (TMSCN) to carbonyl compound