Unusually facile solvolysis of primary tosylates. A case for participation by the N-nitroso group

SR Koepke, R Kupper, CJ Michejda

Index: Koepke,S.R. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 15 p. 2718 - 2722

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Citation Number: 38

Abstract

The acetolysis of the primary tosylates, N-methyl-N-nitroso-2-(tosyloxy) ethylamine (1) and N- methyl-N-nitroso-3-(tosyloxy) propylamine (2), gives the corresponding acetates in better than 80% isolated yields. The kinetic analysis of the acetolysis reactions indicated very rapid solvolysis. The activation parameters for 1 are 0= 17 kcal/mol and AS $=-16.6 eu, and for 2 they are 0= 18.5 kcal/mol and AS*=-21 eu. Acetolysis of the optically active secondary ...