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Microwave-assisted reactions of $\alpha$-diazoketones with hetaryl and ferrocenyl thioketones


Mloston, Grzegorz; Hamera-Faldyga, Roza; Jeske, Malgorzata; Godziszewska, Magdalena; Urbaniak, Katarzyna; Heimgartner, Heinz (2017). Microwave-assisted reactions of $\alpha$-diazoketones with hetaryl and ferrocenyl thioketones. Journal of Sulfur Chemistry:Epub ahead of print.

Abstract

Differently substituted hetaryl thioketones react with less reactive diazoketones under MW irradiation in toluene solution. After only 2 min, the reactions were complete and, depending on the type of the used diazoketone, α,β-unsaturated ketones, acyl substituted thiiranes or 1,3-oxathiols were obtained as final products. In the case of azibenzil and di(thiophen-2-yl) thioketone, a new type of 1,5-dipolar electrocyclization of the intermediate thiocarbonyl ylide involving a thiophene ring led to a fused sulfur heterocycle. In contrast to hetaryl thioketones, the ferrocenyl analogues decompose under MW irradiation. Alternatively they react with diazopropanone and 2-diazo-1-phenylethanone in boiling THF in the presence of LiClO4 to give α,β-unsaturated ketones as sole products. In these cases, the reactions require long reaction times.

Abstract

Differently substituted hetaryl thioketones react with less reactive diazoketones under MW irradiation in toluene solution. After only 2 min, the reactions were complete and, depending on the type of the used diazoketone, α,β-unsaturated ketones, acyl substituted thiiranes or 1,3-oxathiols were obtained as final products. In the case of azibenzil and di(thiophen-2-yl) thioketone, a new type of 1,5-dipolar electrocyclization of the intermediate thiocarbonyl ylide involving a thiophene ring led to a fused sulfur heterocycle. In contrast to hetaryl thioketones, the ferrocenyl analogues decompose under MW irradiation. Alternatively they react with diazopropanone and 2-diazo-1-phenylethanone in boiling THF in the presence of LiClO4 to give α,β-unsaturated ketones as sole products. In these cases, the reactions require long reaction times.

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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:14 August 2017
Deposited On:24 Aug 2017 15:17
Last Modified:24 Aug 2017 15:17
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland) (Grant Maestro-3 (Dec-2012/06/A/ST5/00219)).
Additional Information:This is an Accepted Manuscript of an article electronically published by Taylor & Francis in Journal of Sulfur Chemistry on 13.08.2017, available online: http://wwww.tandfonline.com/10.1080/17415993.2017.1363206.
Publisher DOI:https://doi.org/10.1080/17415993.2017.1363206

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