The reaction of substituted glycols with catalytic dibutyltin oxide, stoichiometric p -toluenesulfonyl chloride, and triethylamine in CH 2 Cl 2 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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Martinelli et al. (1999) studied this question.
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