Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones: Important Building Blocks in Tetrathiafulvalene Chemistry

Jeppe Granhøj; Viktor Bliksted Roug Pedersen; Peter Lundgård Krøll; Line Broløs; Mogens Brøndsted Nielsen

doi:10.1021/acs.joc.3c01369

Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones: Important Building Blocks in Tetrathiafulvalene Chemistry

Jeppe Granhøj, Viktor Bliksted Roug Pedersen, Peter Lundgård Krøll, Line Broløs, Mogens Brøndsted Nielsen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

2 Citations (Scopus)

Abstract

2-(Methylthio)-1,3-dithioles are important heterocyclic compounds used for the preparation of redox-active derivatives of tetrathiafulvalene as they serve as precursors for phosphonate esters that can be employed in Horner-Wadsworth-Emmons olefination reactions. Here, we present a mild and less hazardous method than previous methods for converting readily accessible 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation with trimethyl orthoformate and HBF₄·Et₂O and a subsequent reduction with NaBH₄

Original language	English
Journal	Journal of Organic Chemistry
Volume	88
Issue number	17
Pages (from-to)	12853-12856
Number of pages	4
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.3c01369
Publication status	Published - 2023

Bibliographical note

Funding Information:
The Novo Nordisk Foundation is acknowledged for supporting this work (Grant No. NNF20OC0061574). We acknowledge Christina Schøttler Nielsen, University of Copenhagen, and Sino-Danish College (SDC), University of Chinese Academy of Sciences, for providing starting materials.

Publisher Copyright:
© 2023 American Chemical Society

Access to Document

10.1021/acs.joc.3c01369

Cite this

Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones : Important Building Blocks in Tetrathiafulvalene Chemistry. / Granhøj, Jeppe; Bliksted Roug Pedersen, Viktor ; Lundgård Krøll, Peter; Broløs, Line; Brøndsted Nielsen, Mogens.

In: Journal of Organic Chemistry, Vol. 88, No. 17, 2023, p. 12853-12856.

Research output: Contribution to journal › Journal article › Research › peer-review

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title = "Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones: Important Building Blocks in Tetrathiafulvalene Chemistry",

abstract = "2-(Methylthio)-1,3-dithioles are important heterocyclic compounds used for the preparation of redox-active derivatives of tetrathiafulvalene as they serve as precursors for phosphonate esters that can be employed in Horner-Wadsworth-Emmons olefination reactions. Here, we present a mild and less hazardous method than previous methods for converting readily accessible 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation with trimethyl orthoformate and HBF4·Et2O and a subsequent reduction with NaBH4",

author = "Jeppe Granh{\o}j and {Bliksted Roug Pedersen}, Viktor and {Lundg{\aa}rd Kr{\o}ll}, Peter and Line Brol{\o}s and {Br{\o}ndsted Nielsen}, Mogens",

note = "Funding Information: The Novo Nordisk Foundation is acknowledged for supporting this work (Grant No. NNF20OC0061574). We acknowledge Christina Sch{\o}ttler Nielsen, University of Copenhagen, and Sino-Danish College (SDC), University of Chinese Academy of Sciences, for providing starting materials. Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

year = "2023",

doi = "10.1021/acs.joc.3c01369",

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T1 - Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones

T2 - Important Building Blocks in Tetrathiafulvalene Chemistry

AU - Granhøj, Jeppe

AU - Bliksted Roug Pedersen, Viktor

AU - Lundgård Krøll, Peter

AU - Broløs, Line

AU - Brøndsted Nielsen, Mogens

N1 - Funding Information: The Novo Nordisk Foundation is acknowledged for supporting this work (Grant No. NNF20OC0061574). We acknowledge Christina Schøttler Nielsen, University of Copenhagen, and Sino-Danish College (SDC), University of Chinese Academy of Sciences, for providing starting materials. Publisher Copyright: © 2023 American Chemical Society

PY - 2023

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N2 - 2-(Methylthio)-1,3-dithioles are important heterocyclic compounds used for the preparation of redox-active derivatives of tetrathiafulvalene as they serve as precursors for phosphonate esters that can be employed in Horner-Wadsworth-Emmons olefination reactions. Here, we present a mild and less hazardous method than previous methods for converting readily accessible 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation with trimethyl orthoformate and HBF4·Et2O and a subsequent reduction with NaBH4

AB - 2-(Methylthio)-1,3-dithioles are important heterocyclic compounds used for the preparation of redox-active derivatives of tetrathiafulvalene as they serve as precursors for phosphonate esters that can be employed in Horner-Wadsworth-Emmons olefination reactions. Here, we present a mild and less hazardous method than previous methods for converting readily accessible 1,3-dithiole-2-thiones into 2-(methylthio)-1,3-dithioles by methylation with trimethyl orthoformate and HBF4·Et2O and a subsequent reduction with NaBH4

U2 - 10.1021/acs.joc.3c01369

DO - 10.1021/acs.joc.3c01369

M3 - Journal article

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AN - SCOPUS:85170089226

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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