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Reactions of carbanions derived from α-substituted-methyl tolyl sulfones with quinone methides as Michael acceptors |
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| Authors: | Gra?yna Groszek Sylwia B?a?ej Dariusz ?wierczyński |
| Affiliation: | a Faculty of Chemistry, Rzeszow University of Technology, 6 Powstancow Warszawy Ave., 35-959 Rzeszow, Poland b Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland c Department of Chemistry, Agricultural University of Cracow, 21 Mickiewicz Ave., 31-120 Cracow, Poland |
| 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. |
| Keywords: | Michael addition α-Halo-4-tolylsulfonyl methyl anions Rearrangement Tosyl migration |
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