Study of reactions leading to sulfine formation. 5. Methoxide-catalyzed decomposition of diarylmethyl (arylsulfonyl) methyl sulfoxides: a sulfine-forming elimination on …

JL Kice, L Kupczyk-Subotkowska

Index: Kice, John L.; Kupczyk-Subotkowska, Lidia Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1424 - 1430

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Abstract

In 7: 3 CH30H-DMS0 (v/v) in the presence of methoxide ion, diarylmethyl (arylsulfony1) methyl sulfoxides (Ar2CHS (O) CH# OAAI) 4, undergo elimination remarkably easily to afford the diarylsulfine and the aryl methyl sulfone (eq 4). Comparison of the rate of cleavage of 4 (keb) and the rate of disappearance of the'H NMR signal (kcHso) for the Ar2CHS (0) proton in CD, OD-DMSO shows that the mechanism for the elimination is on the (ElcB),,/(ElcB) ...