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Reactions of (aryl)(chloro)methyl p-tolyl sulfoxides with tetrasulfur tetranitride (S4N4): Formation and characterization of 3,5-diaryl-1,2,4,6-thiatriazine 1-oxides

Authors
Kong, YCKim, KPark, YJ
Issue Date
Sep-2000
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
tetrasulfur tetranitride; alpha-chloro sulfoxides; thiatriazine 1-oxides; triazines
Citation
TETRAHEDRON, v.56, no.37, pp 7153 - 7161
Pages
9
Journal Title
TETRAHEDRON
Volume
56
Number
37
Start Page
7153
End Page
7161
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16739
DOI
10.1016/S0040-4020(00)00632-3
ISSN
0040-4020
Abstract
The reactions of (aryl)(chloro)methyl p-tolyl sulfoxides 2 with tetrasulfur tetranitride (S4N4) in p-dioxane at reflux gave 3,5-diaryl-1,2,4,6-thiatriazine 1-oxides, 3,5-diaryl-1,2,4-thiadiazoles, and 1-amino-3,5-diaryl-1,2,4,6-thiatriazine 1-oxides. For the first time, the structures of 3,5-diaryl-1,2,4,6-thiatriazine 1-oxides were unequivocally characterized based on X-ray crystallography of 3,5-di(3,4-dimethylphenyl)-1,2,4,,6-thiatriazine 1-oxide. Treatment of the thiatriazine 1-oxides with m-CPBA gave 2,6-diaryl-4-(3-chlorophenyl)-1,3,5-triazines. Mechanisms are proposed for the formation of thiatriazine 1-oxides and 1,3,5-triazines. (C) 2000 Elsevier Science Ltd. All rights reserved.
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