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Reaction of selenium and tellurium halides with propargyl alcohols. The regio‐ and stereoselectivity of addition to the triple bond
Author(s) -
Braverman Samuel,
Cherkinsky Marina,
Jana Ranjan,
Kalendar Yuliya,
Sprecher Milon
Publication year - 2010
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1729
Subject(s) - chemistry , stereospecificity , triple bond , selenium , propargyl , stereoselectivity , halide , organic chemistry , stereochemistry , medicinal chemistry , double bond , catalysis
A convenient method to incorporate selenium into an organic molecule is reported. Various aspects of the reaction of SeCl 2 with propargyl alcohols, i.e., identity of reacting functionality, regiospecificity, and stereospecificity, differ from expectations based on known reactions of these alcohols with SCl 2 . Selenium dihalides undergo smooth 1,2‐addition to the triple bond of various propargylic alcohols resulting in the formation of the corresponding functionalized divinyl selenides in high yields and with complete regio‐ and stereospecificity. Of special mechanistic interest is the syn ‐addition and anti‐Markovnikov orientation observed in all cases. Copyright © 2010 John Wiley & Sons, Ltd.