Dibutyltin oxide catalyzed selective sulfonylation of alpha-chelatable primary alcohols

Authors
Martinelli, MJ Nayyar, NK Moher, ED Dhokte, UP Pawlak, JM Vaidyanathan, R
Citation
Mj. Martinelli et al., Dibutyltin oxide catalyzed selective sulfonylation of alpha-chelatable primary alcohols, ORG LETT, 1(3), 1999, pp. 447-450
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
3
Year of publication
1999
Pages
447 - 450
Database
ISI
SICI code
1523-7060(19990812)1:3<447:DOCSSO>2.0.ZU;2-1
Abstract
The reaction of substituted glycols with catalytic dibutyltin oxide, stoich iometric p-toluenesulfonyl chloride, and triethylamine in CH2Cl2 resulted i n the complete and rapid sulfonylation at the primary alcohol, The alpha-he terosubstituted primary alcohol moiety appeared optimal for best results, s upporting the intermediacy of a five-membered chelate, The role of the amin e is discussed, in addition to catalyst requirements and solvent effects.