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Communication | Regular issue | Vol 53, No. 8, 2000, pp.1669-1675
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8904
Bis[oxo/thioxothiazolinyl] Aromatic Compounds — Stereochemical Aspects

Anca Hîrtopeanu, Marina Mihai, Gheorghe Mihai, and Christian Roussel*

*E.N.S.S.P.I.C.A.M., Avenu Escadrille Normandie-Niemen, 13397 Mareseille Cedex 20, France

Abstract

The geometry, equilibrium compositions and barriers to rotation for the bis[oxo/thioxothiazolinyl] aromatic compounds (1-4), a series of atropisomers with two stereogenic C(aryl) - N(heterocycle) axes are reported. Comparison of the experimentally determined barriers to rotation provides information about the electronic and steric substituent contributions to the barriers, as in the series there is variation of dipoles and of substituents on the heterocyclic or the aromatic part.