Bulletin of the Chemical Society of Japan

Ring Opening of Oxiranes by Trimethylsilyl Trifluoromethanesulfonate

S Murata, M Suzuki, R Noyori

Index: Murata, Sizuaki; Suzuki, Masaaki; Noyori, Ryoji Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 1 p. 247 - 254

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Citation Number: 35

Abstract

Trimethylsilyl trifluoromethanesulfonate promotes ring opening reactions of oxirane derivatives. The reaction course is highly affected by the structures and substitution pattern of the substrates. Tetra-, tri-, and 2, 2-disubstituted oxiranes and simple cycloalkene oxides are converted to the corresponding allylic alcohol trimethylsilyl ethers. The overall transformation is interpreted in terms of trans addition of the silyl trifluoromethanesulfonate ...