γ-and δ-epoxy sulfones. Formation of different ring-sized products upon reaction with CH3MgI or LiN [CH (CH3) 2] 2

JM Decesare, B Corbel, T Durst…

Index: Decesare, John M.; Corbel, Bernard; Durst, Tony; Blount, John F. Canadian Journal of Chemistry, 1981 , vol. 59, p. 1415 - 1424

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Citation Number: 24

Abstract

γ-Epoxy sulfones in which the epoxide function is terminal yield cyclopropylmethanol derivatives on reaction with methyllithium or lithium diisopropylamide. In contrast, treatment of these epoxides with two equivalents of CH3MgI gives only cis-3- phenylsulfonylcyclobutanols. The cis-relationship between the OH and sulfonyl groups was proven in one instance by an X-ray structure determination. Internal γ-epoxy sulfones yield ...

~83%

~75%

~90%

~45%

~86%

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