Chalcogen Halides Plus Propargyl Alcohols—Fascinating Reaction Pathways and Products

Abstract

A convenient method to incorporate selenium into an organic molecule is reported. Selenium halides undergo smooth 1,2-addition to the triple bond of various propargylic alcohols under mild reaction conditions and with complete regio- and stereospecificity. The products arising from these reactions depend on the nature of the selenium halide as well as on the substitution pattern of the propargyl alcohol. Of special mechanistic interest is the syn-addition and anti-Markovnikov orientation observed in all cases.

Keywords:

• Divinyl selenides
• electrophilic addition
• regioselectivity
• selenium dichloride
• selenium tetrachloride
• stereoselectivity

Acknowledgments

This work was supported by a grant from the Israel Science Foundation (Grant No. 919-05).