Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity

C Adam, L García-Río, JR Leis, JA Moreira

Index: Adam; Garcia-Rio; Leis; Moreira Tetrahedron, 2006 , vol. 62, # 37 p. 8822 - 8829

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Citation Number: 3

Abstract

The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (αlg≈− 1.30), but virtually independent of the basicity of the thiol (βnuc≈ 0.10). This dependence is ascribed to the presence of a nucleophile desolvation equilibrium (βd) that is followed by the attack of the thiolate ion on the nitroso group (βnuc′) via a concerted ...