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Synthesis and Structure of a Dispirocyclic 1,3-Dithiolane-S-oxide


Mloston, Grzegorz; Heimgartner, Heinz (1995). Synthesis and Structure of a Dispirocyclic 1,3-Dithiolane-S-oxide. Polish Journal of Chemistry, 69:1649-1654.

Abstract

The reaction of a 2,5-dihydro-1,3,4-thiadiazole and a sulfine in THF at 50°C yields a 1,3-dithiolane-S-oxide as the major product. The formation of the latter is rationalized by the 1,3-dipolar cycloaddition of a thiocarbonyl-S-ylide, generated by thermal N2-elimination from the corresponding 2,5-dihydro-1,3,4-thiadiazole, onto the sulfine (C=S)-bond. The structure of the dispirocyclic 1,3-dithiolane-S-oxide has been established by X-ray crystallography.

Abstract

The reaction of a 2,5-dihydro-1,3,4-thiadiazole and a sulfine in THF at 50°C yields a 1,3-dithiolane-S-oxide as the major product. The formation of the latter is rationalized by the 1,3-dipolar cycloaddition of a thiocarbonyl-S-ylide, generated by thermal N2-elimination from the corresponding 2,5-dihydro-1,3,4-thiadiazole, onto the sulfine (C=S)-bond. The structure of the dispirocyclic 1,3-dithiolane-S-oxide has been established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1995
Deposited On:04 Dec 2013 13:25
Last Modified:05 Apr 2016 17:12
Publisher:Polskie Towarzystwo Chemiczne
ISSN:0137-5083
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel

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