Stereochemistry in trivalent nitrogen compounds. 42. N-(Arylthio) benzimidazoles. Torsional barriers and 1, 3 rearrangement

…, H Chang, L Craine, E Hortelano

Index: Raban, Morton; Chang, Hu; Craine, Leslie; Hortelano, Edwin Journal of Organic Chemistry, 1985 , vol. 50, # 13 p. 2205 - 2210

Full Text: HTML

Citation Number: 49

Abstract

A series of N-[(2, 4dinitrophenyl) thio] benzimidazoles has been prepared by reaction of 2, 4dinitrobenzenesulfenyl chloride with a series of 2-alkylbenzimidazoles and 5 (6)-chloro-2- alkylbenzimihlea. Dynamic NMR spectroscopy was used to measure the torsional barriers about the NS bonds, which were in the range of ca. 19-20 kcal/mol. In one case, diastereomeric transformation and conventional kinetics were used to obtain an ...