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Oxidation of cis-3,5-di-tert-alkyl-3,5-diphenyl-1,2,4-trithiolanes: isolation and some properties of the 1-oxides and the 1,2-dioxides

✍ Scribed by Hideaki Oshida; Akihiko Ishii; Juzo Nakayama


Book ID
104251431
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
204 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


Oxidation of cis-3,5-di-tert-alkyl-3,5-diphenyl-1,2,4

-trithiolane with an excess amount of dimethyldioxirane gave the 1,2-dioxide, a vic-disulfoxide, and it was verified that the 1,2-dioxide was formed specifically from one of two stereoisomeric monoxides. The structures of the monoxides and the 1,2-dioxide were determined by X-ray crystallography.


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3,4-Diphenyl-1,2,5-thiadiazole 1-oxide (1a) in acetonitrile solution is electroreduced to 2,4,6-triphenyl-1,3,5triazine and 3,4-diphenyl-1,2,5-thiadiazole. This behavior is very different from that of similar compounds with other oxidation states of the heterocyclic sulfur atom, such as the 1,1-diox