Structural Effects on the Transition States of Imine-Forming Eliminations in N-Substituted O-(Arylsulfonyl)hydroxylamines

Article abstract of DOI:10.1021/ja00220a048

A series of amines with various alkyl and aryl substituents at C-1 were converted to the corresponding N-(arylsulfonoxy)amines, which served as precursors for base-promoted, imine-forming elimination.By varying the bases used to promote the elimination and by varying the leaving groups attached to nitrogen, the Broensted parameters β and β_lg^CH3 were determined.These were used to locate the transition state on the More O'Ferrall-Jencks energy surface for elimination.Substituents were found to influence the structure of the activated complex markedly.Resonance effects were most important, while inductive effects had little influence .