Tetrahedron Letters

Thermolysis of 1, 3-dithiol-2-yl azides and thermal properties of the resulting 1, 4, 2-dithiazines

J Nakayama, A Sakai, A Tokiyama, M Hoshino

Index: Nakayama, Juzo; Sakai, Atsuhiro; Tokiyama, Akira; Hoshino, Masamatsu Tetrahedron Letters, 1983 , vol. 24, # 35 p. 3729 - 3732

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Citation Number: 17

Abstract

Abstract 2-Substituted 1, 3-dithiol-2-yl azides, on thermolysis in refluxing toluene, give 3- substituted 1, 4, 2-dithiazines which thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1, 3-dithiol-2-yl azides undergo both ring expansion yielding 1, 4, 2-dithiazines and peculiar thermal dissociation into 1, 3-dithiol-2-ylidene carbenes and hydrogen azide.