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Direct Access to N-Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure

Carl Albrecht Dannenberg, Vincent Bizet, Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, Email: carsten.bolmoc.rwth-aachen.de

C. A. Dannenberg, V. Bizet, C. Bolm, Synthesis, 2015, 47, 1951-1959.

DOI: 10.1055/s-0034-1380536 (free Supporting Information)


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Abstract

In a preparation of N-alkyl-substituted sulfoximines from sulfides, in situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the desired products. This unprecedented one-pot imidation/oxidation sequence provides gram quantities of product in a short period of time avoiding the use of toxic alkylating reagents.

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Key Words

sulfoximine, imidation, oxidation, synthetic method, sulfide. potassium permanganate


ID: J66-Y2015