The reaction of some propargyl alcohols with benzeneselenenyl chloride

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Abstract
The reaction of benzeneselenenyl chloride with twenty-two propargyl alcohols in methylene chloride solution is reported. Products of both Markownikoff and anti-Markownikoff regiochemistry are formed in an anti stereospecific manner. The regioselectivity or specificity is found to be very dependent upon the nature of the substituents geminal to the alcoholic moiety. In general the presence of bulky substituents geminal to the alcoholic moiety tend to favour formation of the anti-Markownikoff adduct under conditions of kinetic control. The Markownikoff adducts are found to be favoured thermodynamically.

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