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Reduction of Thiocarbonyl Compounds with Lithium Diisopropylamide


Gebert, Andreas; Jasinski, Marcin; Mloston, Grzegorz; Heimgartner, Heinz (2014). Reduction of Thiocarbonyl Compounds with Lithium Diisopropylamide. Helvetica Chimica Acta, 97(7):931-938.

Abstract

Treatment of 4,4-disubstituted 2-phenyl-1,3-thiazole-5(4H)-thiones with lithium diisopropylamide (LDA; LiNiPr2) in THF at -78° yielded the corresponding 1,3-thiazole-5(4H)-thioles in moderate yields. Sequential treatment with LDA and MeI under the same conditions led to the 5-methylsulfanyl derivatives. Similarly, reaction of some cycloalkanethiones as well as diaryl thioketones with LDA and MeI gave cycloalkyl methyl sulfides and diarylmethyl methyl sulfides, respectively. A reaction mechanism via H transfer from LDA to the thiocarbonyl C-atom via a six-membered transition state is proposed for this unprecedented reduction of the C1⁄4S bond.

Abstract

Treatment of 4,4-disubstituted 2-phenyl-1,3-thiazole-5(4H)-thiones with lithium diisopropylamide (LDA; LiNiPr2) in THF at -78° yielded the corresponding 1,3-thiazole-5(4H)-thioles in moderate yields. Sequential treatment with LDA and MeI under the same conditions led to the 5-methylsulfanyl derivatives. Similarly, reaction of some cycloalkanethiones as well as diaryl thioketones with LDA and MeI gave cycloalkyl methyl sulfides and diarylmethyl methyl sulfides, respectively. A reaction mechanism via H transfer from LDA to the thiocarbonyl C-atom via a six-membered transition state is proposed for this unprecedented reduction of the C1⁄4S bond.

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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 2014
Deposited On:18 Jul 2014 08:46
Last Modified:08 Dec 2017 18:25
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, National Science Center (Cracow, Poland)
Publisher DOI:https://doi.org/10.1002/hlca.201400130

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