Selenium stabilized carbanions. Preparation of. alpha.-lithio selenides and applications to the synthesis of olefins by reductive elimination of. beta.-hydroxy selenides …

HJ Reich, F Chow, SK Shah

Index: Reich,H.J. et al. Journal of the American Chemical Society, 1979 , vol. 101, p. 6638 - 6648

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Citation Number: 94

Abstract

Abstract: The deprotonation of several alkyl aryl selenides with lithium amide bases has been studied. The kinetic acidity of methyl m-trifluoromethylphenyl selenide was found to be 1/33 that of the sulfur analogue. The introduction of a m-trifluoromethyl substituent into methyl phenyl sulfide increased the kinetic acidity by a factor of 22.4. A variety of@-hydroxy selenides have been prepared by the reduction of a-phenylseleno ketones and the ...