Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with 
quinone methides as Michael acceptors

Groszek, G; Blazej, S; Brud, AJ; Swierczynski, D; Lemek, T

doi:10.1016/j.tet.2005.12.040

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Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with quinone methides as Michael acceptors

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https://www.sciencedirect.com/science/article/pii/S0040402005022088
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Groszek, G., Blazej, S., Brud, A., Swierczynski, D., & Lemek, T. (2006). Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with quinone methides as Michael acceptors. Tetrahedron, 62(11), 2622-2630. doi:10.1016/j.tet.2005.12.040.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0013-D26F-F

Abstract

Nucleophilic addition of α-halo-4-tolylsulfonyl methyl anions to quinone methides and subsequent reactions were studied. Three kinds of consecutive reaction products were isolated, depending on the substrate structures and reaction conditions. Two of them were identified as rearrangement products and one as the vicarious nucleophilic substitution (VNS) product. An unexpected 1,2-migration of the tosyl group was observed. The mechanism of the reactions is briefly discussed.