71069-25-5Relevant academic research and scientific papers
Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight
Martinelli, Michael J.,Vaidyanathan, Rajappa,Pawlak, Joseph M.,Nayyar, Naresh K.,Dhokte, Ulhas P.,Doecke, Christopher W.,Zollars, Lisa M. H.,Moher, Eric D.,Khau, Vien Van,Kosmrlj, Berta
, p. 3578 - 3585 (2002)
This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.
Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols
Martinelli, Michael J.,Nayyar, Naresh K.,Moher, Eric D.,Dhokte, Ulhas P.,Pawlak, Joseph M.,Vaidyanathan, Rajappa
, p. 447 - 450 (2008/02/11)
(equation presented) 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.
