New stereoselective routes from alcohols to secondary alkyl bromides with retention of configuration

M Sevrin, A Krief

Index: Sevrin, Mireille; Krief, Alain Journal of the Chemical Society, Chemical Communications, 1980 , # 14 p. 656 - 657

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Citation Number: 14

Abstract

Summary Secondary alcohols can be converted into the corresponding bromides with high stereoselective reten- tion of configuration ; this two-step process proceeds by a double inversion involving the intermediate selenides . ... WE report here a new method for converting secondary alcohols (A) into the corresponding alkyl bromides (C)ls2 ... R2 R2 (i 1, PhSeCN - Bu3P R1hkoH or (ti), MeS02Cl thz P h Se sv R' H PhSeNa H (A) (8) ... Yield/ % (method) 74 (i) 70 (ii) 79 (ii) ...