Meisenheimer rearrangement of methoxymethyl phenyl sulfoxide. Formation and disproportionation of methoxymethyl benzenesulfenate

TJ Maricich, CK Harrington

Index: Maricich,T.J.; Harrington,C.K. Journal of the American Chemical Society, 1972 , vol. 94, p. 5115 - 5116

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Citation Number: 19

Abstract

The Meisenheimer rearrangement of amine N-oxides to substituted hydroxylamines invariably favors the N-+ 0 1, 2 shift2 In sharp contrast with this are the generally preferred thermal 0-+ S 1, 2 shifts of the sulfoxylate+~ ulfinate,~ sulfinate+~ ulfone,~ and sulfenate+ sulfoxide5 rearrangements, as well as the thermal 0+ P 1, 2 shift in the phosphinite+ phosphine oxide rearrangement. 6