Tetrahedron

Synthesis of structurally modified atropisomeric biaryl dithiols. Observations on the Newman-Kwart rearrangement

S Cossu, O De Lucchi, D Fabbri, G Valle, GF Painter…

Index: Cossu, Sergio; De Lucchi, Ottorino; Fabbri, Davide; Valle, Giovanni; Painter, Gavin F.; Smith, Robin A.J. Tetrahedron, 1997 , vol. 53, # 17 p. 6073 - 6084

Full Text: HTML

Citation Number: 45

Abstract

The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3, 3′- disubstituted dithiols via ortho metallation are presented. The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical ...