Tetrahedron

Hindered rotation in N-acyloxy-4-methylthiazole-2 (3H)-thiones

J Hartung, C Schur, I Kempter, S Altermann, G Stapf…

Index: Hartung, Jens; Schur, Christine; Kempter, Irina; Altermann, Sabine; Stapf, Georg; Bergstraesser, Uwe; Gottwald, Thomas; Heubes, Markus Tetrahedron, 2009 , vol. 65, # 36 p. 7527 - 7532

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Citation Number: 5

Abstract

Experimentally determined barriers to O-acyl group topomerization in mixed anhydrides composed of β-disubstituted carboxylic acids and cyclic thiohydroxamic acid N-hydroxy-4- methylthiazole-2 (3H)-thione were located in the range of ΔG‡ 320= 68±8kJmol− 1 (DNMR). According to modeling studies, the underlying exchange process is proposed to occur via rotation about the N, O bond for torsional movement of the O-acyl group past the ...