Halogenations of S-Benzyl-S-phenylsulfoximides and Base-induced Rearrangements of Their N- and α-Halo Derivatives to N-Sulfinylimines

概要

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The reactions of S-benzyl-and S-(p-nitrobenzyl) sulfoximides 1a, b with N-bromosuccinimide or tert-butyl hypochlorite gave the corresponding N-halosulfoximides 2a, b or 3a, b, respectively, in good yields. The N-bromo-S-(p-nitrobenzyl) sulfoximide 2b decomposed in the presence of a light source to give the corresponding α-bromosulfoximide 4b, whereas the other N-halosulfoximides 2a and 3a, b did not give the corresponding α-halosulfoximides 4a and 5a, b. On treatment with N-chlorosuccinimide, the p-nitrobenzyl-sulfoximide 1b underwent both N- and α-chlorinations, while the benzylsufoximide 1a underwent only N-chlorination. The halosulfoximides 2-5 underwent base-induced rearrangements under various conditions to give the corresponding N-sulfinylimines 6 via the same three-membered cyclic sulfoximide intermediate, a thiazirine S-oxide 8.
公益社団法人日本薬学会の論文
1982-12-25