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The unusual influence of hetaryl groups on the direct conversion of some secondary alcohols into thiols with Lawesson’s reagent: elucidation of the reaction mechanism


Mloston, Grzegorz; Hamera-Faldyga, Roza; Celeda, Malgorzata; Linden, Anthony; Heimgartner, Heinz (2017). The unusual influence of hetaryl groups on the direct conversion of some secondary alcohols into thiols with Lawesson’s reagent: elucidation of the reaction mechanism. Journal of Sulfur Chemistry, 38(5):475-487.

Abstract

A series of hetaryl-substituted methanols were used for direct conversion into the corresponding thiols by treatment with Lawesson’s reagent in boiling toluene. Unexpectedly, the respective sulfides were formed exclusively. In the case of chiral alcohols, the sulfides were obtained as 1:1-mixtures of meso- and dl-diastereoisomers. In contrast to hetaryl-substituted alcohols, the analogous protocol applied for benzhydryl alcohol led to a mixture of the expected secondary thiol and a bis(diphenylmethyl) trithiophosphonate. Finally, the analogous reactions with ferrocenyl(phenyl)methanol and diferrocenylmethanol, respectively, led to the corresponding thiols in good yield.

Abstract

A series of hetaryl-substituted methanols were used for direct conversion into the corresponding thiols by treatment with Lawesson’s reagent in boiling toluene. Unexpectedly, the respective sulfides were formed exclusively. In the case of chiral alcohols, the sulfides were obtained as 1:1-mixtures of meso- and dl-diastereoisomers. In contrast to hetaryl-substituted alcohols, the analogous protocol applied for benzhydryl alcohol led to a mixture of the expected secondary thiol and a bis(diphenylmethyl) trithiophosphonate. Finally, the analogous reactions with ferrocenyl(phenyl)methanol and diferrocenylmethanol, respectively, led to the corresponding thiols in good yield.

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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:April 2017
Deposited On:25 Apr 2017 12:41
Last Modified:09 Dec 2017 00:45
Publisher:Taylor & Francis
ISSN:1741-5993
Publisher DOI:https://doi.org/10.1080/17415993.2017.1313257

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