Rearrangement Reaction Based on the Structure of N-Fluoro- N-alkyl Benzenesulfonamide.

J Org Chem

Key Lab for Advanced Material & Institute of Fine Chemicals , East China University of Science and Technology, 130 Meilong Road , Shanghai 200231 , China.

Published: November 2018

A novel rearrangement reaction based on the structure of N-fluoro- N-alkyl benzenesulfonamide was developed. The reaction proceeded readily at 50 °C in formic acid and generated a variety of benzenesulfonamides and aldehydes or ketones simultaneously. The reaction mechanism is believed to be a concerted mechanism that consist of 1,2-aryl migration with the departure of fluorine anion via an S2 mechanism. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operations, and a broad substrate scope.

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http://dx.doi.org/10.1021/acs.joc.8b01841DOI Listing

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