Behavior of benzyl sulfoxides toward acid chlorides. Useful departures from the Pummerer reaction

JP Chupp, TM Balthazor, MJ Miller…

Index: Chupp, John P.; Balthazor, Terry M.; Miller, Michael J.; Pozzo, Mark J. Journal of Organic Chemistry, 1984 , vol. 49, p. 4711 - 4716

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Citation Number: 13

Abstract

Close inspection of this reaction reveals that prior to product formation, a cyclic sulfilimine salt 3 is formed by loss of water. These salts are known materials, quite analogous to the acyclic variety alluded to earlier, and usually formed by an oxidative ring closure of an o- aminobenzyl methyl sulfide. 25 As with other sulfilimines, the presence of electron- withdrawing substituents renders them more stable, with the free base isolable in the case ...