The oxidation of amines with sulfonyl peroxides. 6. Transition-state structures of base-promoted, imine-forming eliminations from N-benzyl-O-(arylsulfonyl) …

RV Hoffman, EL Belfoure

Index: Hoffman, Robert V.; Belfoure, Edward L. Journal of the American Chemical Society, 1982 , vol. 104, # 8 p. 2183 - 2189

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Abstract

Abstract: Eliminations in XC6H4CH2NHOS02C6H4Y promoted by amine bases were examined in 2.25 MH 2 0 in THF-EtOAc (3: l) and methanol. Transition-state parameters in methanol were found to be p= 0.1 1, kH/kD= 1.2, for the benzylic group and p= 1.65 for the leaving group. These data indicate that the polar solvent methanol causes an El-like transition state in this elimination. Brernsted parameters were determined for both solvents ...