Author:
Kong Xianqi,Grindley T. Bruce
Abstract
The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the nature of the alkyl group on tin, the solvent, and the reaction temperature. Virtually all dibutylstannylene acetals react preferentially on the primary oxygen atom, sometimes with excellent regioselectivity. Increasing the steric bulk of the alkyl substituents on tin increases the preference for reaction at the secondary oxygen atom, but at the expense of increased reaction times. Hexamethylenestannylene acetals react at about the same rate as dibutylstannylene acetals; in almost all cases, they react preferentially on the secondary oxygen atom, sometimes with excellent regioselectivity.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
34 articles.
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