Reactivity patterns of N-methylbenzhydroxamates. I. Studies of methyl transfer between N-methylbenzhydroxamates and arenesulfonates

KR Fountain, DP Fountain, B Michaels…

Index: Fountain, Kenneth R.; Fountain, Daniel P.; Michaels, Bernice; Myers, D. Brenton; Salmon, Jon K.; et al. Canadian Journal of Chemistry, 1991 , vol. 69, # 5 p. 798 - 810

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Citation Number: 15

Abstract

The rates of methyl transfer between benzohydroxamates and sulfonates show large βnuc values (ca. 0.8) indicating much charge transfer to the C atom, similar to the results of N, N- dialkylaminofluorene anions. A small α effect shows that even in methyl substrates, with certain leaving groups, the effect is displayed. Investigation of the β1g shows that from the leaving group side of the reaction it is a normal SN2 reaction. Correlation of the reactivity ...