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First synthesis of gem-difluorothiiranes from cycloaliphatic thioketones and difluorocarbene


Mloston, Grzegorz; Romanski, Jaroslaw; Heimgartner, Heinz (1999). First synthesis of gem-difluorothiiranes from cycloaliphatic thioketones and difluorocarbene. Heterocycles, 50:403-410.

Abstract

The reaction of sterically crowded cycloaliphatic thioketones with phenyl(trifluoromethyl)mercury and sodium iodide in boiling benzene yielded gem-difluorothiiranes in fair yields whereas in the case of aromatic thioketones gem-difluoroalkenes were obtained. The formation of these products is rationalized by an addition of difluorocarbene onto the C,S-double bond, followed by the extrusion of sulfur.

The reaction of sterically crowded cycloaliphatic thioketones with phenyl(trifluoromethyl)mercury and sodium iodide in boiling benzene yielded gem-difluorothiiranes in fair yields whereas in the case of aromatic thioketones gem-difluoroalkenes were obtained. The formation of these products is rationalized by an addition of difluorocarbene onto the C,S-double bond, followed by the extrusion of sulfur.

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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:1999
Deposited On:05 Nov 2013 16:30
Last Modified:05 Apr 2016 17:06
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La roche AG, Basel
Permanent URL: https://doi.org/10.5167/uzh-84355

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