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Synthesis of ferrocenyl thioketones and their reactions with diphenyldiazomethane


Mloston, Grzegorz; Hamera, Roza; Heimgartner, Heinz (2015). Synthesis of ferrocenyl thioketones and their reactions with diphenyldiazomethane. Phosphorus, Sulfur, and Silicon and the Related Elements, 190(12):2125-2133.

Abstract

A series of ferrocenyl ketones was obtained via Friedel-Crafts acylation with mixed anhydrides using ferrocene as a nucleophilic agent or ferrocene carboxylic acid as a precursor of the electrophilic species. The ketones obtained thereby undergo smooth thionation (THF, 65 ºC) with Lawesson’s reagent. The ferrocenyl thioketones react with diphenyldiazomethane via N2 elimination to afford the hitherto unknown ferrocenyl-substituted thiiranes.

Abstract

A series of ferrocenyl ketones was obtained via Friedel-Crafts acylation with mixed anhydrides using ferrocene as a nucleophilic agent or ferrocene carboxylic acid as a precursor of the electrophilic species. The ketones obtained thereby undergo smooth thionation (THF, 65 ºC) with Lawesson’s reagent. The ferrocenyl thioketones react with diphenyldiazomethane via N2 elimination to afford the hitherto unknown ferrocenyl-substituted thiiranes.

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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:December 2015
Deposited On:18 Dec 2015 15:07
Last Modified:11 Dec 2016 01:00
Publisher:Taylor & Francis
ISSN:1042-6507
Funders:National Science Center (PL-Cracow) (Grant Maestro-3; Dec-2012/06/A/ST5/00219)
Additional Information:Special Issue: Robert Holmes Special Issue This is an Accepted Manuscript of an article published by Taylor & Francis in [Phosphorus, Sulfur, and Silicon and the Related Elements] on [10 Dec 2015], available online: http://wwww.tandfonline.com/ 10.1080/10426507.2015.1071817.
Publisher DOI:https://doi.org/10.1080/10426507.2015.1071817

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