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Reactions of alpha-diazocamphor with aromatic thioketones


Mloston, Grzegorz; Celeda, Malgorzata; Linden, Anthony; Heimgartner, Heinz (2006). Reactions of alpha-diazocamphor with aromatic thioketones. Heterocycles, 68:33-45.

Abstract

The reactions of α-diazocamphor (6) with aromatic thioketones (9a-d) in dichloromethane at room temperature afforded mixtures of the stereoisomeric spirocyclic thiiranes (10) and (11). A reaction mechanism via [2+3] cycloaddition to give the spirocyclic 2,5-dihydro-1,3,4-thiadiazoles (13) and (14), subsequent elimination of nitrogen and 1,3-dipolar electrocyclization of the intermediate thiocarbonyl ylide (15) is proposed. The structure of the stereoisomers (10a) and (11a) has been established by X-Ray crystallography. Desulfurization of the mixtures (10/11) with triphenylphosphane in boiling THF yielded the alkylidene derivatives (12).

The reactions of α-diazocamphor (6) with aromatic thioketones (9a-d) in dichloromethane at room temperature afforded mixtures of the stereoisomeric spirocyclic thiiranes (10) and (11). A reaction mechanism via [2+3] cycloaddition to give the spirocyclic 2,5-dihydro-1,3,4-thiadiazoles (13) and (14), subsequent elimination of nitrogen and 1,3-dipolar electrocyclization of the intermediate thiocarbonyl ylide (15) is proposed. The structure of the stereoisomers (10a) and (11a) has been established by X-Ray crystallography. Desulfurization of the mixtures (10/11) with triphenylphosphane in boiling THF yielded the alkylidene derivatives (12).

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Additional indexing

Other titles:Reactions of α-Diazocamphor with Aromatic Thioketones
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2006
Deposited On:23 Jul 2012 12:26
Last Modified:05 Apr 2016 15:53
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Polish State Committee for Scientific Research (grant KBN No. 4 T09A 046 25), F. Hoffmann-La Roche AG, Basel
Permanent URL: https://doi.org/10.5167/uzh-63510

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