Structure of (+)-[S-(E)]-N-(alpha-methylbenzylidene)-p-toluenesulfinamide

Abstract

C15H15NOS, Mr = 257.35, monoclinic, P2(1), a = 7.710 (2), b = 5.903 (5), c = 14.700 (3) A, beta = 91.48 (2) degrees, V = 668.8 (6) A3, Z = 2, Dx = 1.278 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 2.18 cm-1, F(000) = 272, T = 296 K, R = 0.043, 944 unique observed reflections. This is the first structure determination of an N-alkylidenesulfinamide. The C = N bond is distorted and lengthened presumably because of the steric interaction and electron-withdrawing effect of the sulfinyl group. The nonplanar conformation is also a result of repulsive steric interaction. The configuration at C = N is trans. The title compound was obtained from the displacement reaction of (-)-1-methyl (S)-p-toluenesulfinate with methyllithium.