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Synthesis of ferrocenyl- and hetaryl-substituted 2,2,2-trifluoroethanols and their conversion into 2,2,2-trifluoroethanethiols using Lawesson’s reagent


Mloston, Grzegorz; Hamera-Faldyga, Roza; Celeda, Malgorzata; Gebicki, Krzystof; Heimgartner, Heinz (2016). Synthesis of ferrocenyl- and hetaryl-substituted 2,2,2-trifluoroethanols and their conversion into 2,2,2-trifluoroethanethiols using Lawesson’s reagent. Journal of Fluorine Chemistry, 188:147-152.

Abstract

Ferrocenyl- and hetaryl-substituted ketones react smoothly with the Ruppert-Prakash reagent and, after desilylation of the intermediate adduct, gave the corresponding tertiary 2,2,2-trifluoroethanols. Similarly, ferrocenyl carbaldehyde was converted into 1-ferrocenyl-2,2,2-trifluoroethanol via nucleophilic trifluoromethylation. Some of the obtained fluorinated alcohols were transformed into thiols by treatment with Lawesson’s reagent or P2S5·2C5H5N complex. Remarkably, the obtained thiols are non-odorous compounds.

Abstract

Ferrocenyl- and hetaryl-substituted ketones react smoothly with the Ruppert-Prakash reagent and, after desilylation of the intermediate adduct, gave the corresponding tertiary 2,2,2-trifluoroethanols. Similarly, ferrocenyl carbaldehyde was converted into 1-ferrocenyl-2,2,2-trifluoroethanol via nucleophilic trifluoromethylation. Some of the obtained fluorinated alcohols were transformed into thiols by treatment with Lawesson’s reagent or P2S5·2C5H5N complex. Remarkably, the obtained thiols are non-odorous compounds.

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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:July 2016
Deposited On:19 Jul 2016 07:18
Last Modified:31 Aug 2016 07:58
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (PL-Cracow) (Grant Maestro-3, Dec-2012/06/A/ST5/00219)
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2016.06.017

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