Selenium stabilized carbanions.. alpha.-Lithio selenoxides as reagents for the synthesis of olefins, allyl alcohols, and dienes

HJ Reich, SK Shah, F Chow

Index: Reich,H.J. et al. Journal of the American Chemical Society, 1979 , vol. 101, p. 6648 - 6656

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Citation Number: 55

Abstract

Abstract: Techniques for the preparation of a-lithio selenoxides have been developed. These reagents react cleanly with most aldehydes and ketones to give 0-hydroxy selenoxides, which can be thermolyzed to allyl alcohols or reduced to &hydroxy selenides, The P-hydroxy selenides are further transformed to olefins by reductive elimination. a-Lithio selenoxides can also be alkylated and acylated, although these reactions are of lesser ...