Stereochemistry of desulfurization of thietane derivatives

BM Trost, WL Schinski, F Chen…

Index: Trost,B.M. et al. Journal of the American Chemical Society, 1971 , vol. 93, p. 676 - 684

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Citation Number: 40

Abstract

Abstract: The preparation of thietanes by pyrolysis of the sodium salt of 1-thiocyanato-3- hydroxypropanes is described. Stereochemistry of fragmentation of the sulfone (induced by pyrolysis) and sulfonium salts (induced by organolithium treatment) to cyclopropanes has been investigated. Both show net crossover, ie, cis-2, 4-dimethyl derivatives producing mainly trans-l, 2-dimethylcyclopropane and trans-2, 4-dimethyl derivatives producing ...