Dibutyltin Oxide Catalyzed Selective Sulfonylation of α-Chelatable Primary Alcohols
Organic Letters1999Vol. 1(3), pp. 447–450
Citations Over TimeTop 10% of 1999 papers
Michael J. Martinelli, Naresh K. Nayyar, Eric D. Moher, Ulhas P. Dhokte, Joseph M. Pawlak, Rajappa Vaidyanathan
Abstract
The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted in the complete and rapid sulfonylation at the primary alcohol. The α-heterosubstituted primary alcohol moiety appeared optimal for best results, supporting the intermediacy of a five-membered chelate. The role of the amine is discussed, in addition to catalyst requirements and solvent effects.
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