Sulfonyl esters 3. The formation of sulfone-sulfonates in the reactions of aryl methanesulfonates with sodium hydride

Sodium hydride reductions of aryl methanesulfonates afford dimeric sulfone-sulfonate esters as well as products arising from SO bond rupture. SO bond rupture becomes more competitive as the LUMO energy of the sulfonate ester declines. Exploration of the chemistry of a sulfone-sulfonate ester reveale...

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Bibliographic Details
Published in:Canadian journal of chemistry 1991-12, Vol.69 (12), p.2127-2135
Main Authors: Baum, James Clayton, Durkin, Kathleen Anne, Precedo, Laura, O'blenes, Stacy Brian, Goehl, John Edward, Langler, Richard Francis, MacCormack, Gerald Kendall, Smith, Lana Louise
Format: Article
Language:English
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Summary:Sodium hydride reductions of aryl methanesulfonates afford dimeric sulfone-sulfonate esters as well as products arising from SO bond rupture. SO bond rupture becomes more competitive as the LUMO energy of the sulfonate ester declines. Exploration of the chemistry of a sulfone-sulfonate ester revealed a complex novel reaction that resulted in the formation of, inter alia, a dichloromethanesulfonate ester and a trichloromethanesulfonate ester. The first successful approaches to the synthesis of the heretofore unknown trichloromethanesulfonates and dichloromethanesulfonates are reported. Key words: sodium hydride reductions, sulfenes, sulfone-sulfonate esters
ISSN:0008-4042
1480-3291
DOI:10.1139/v91-307