TY - JOUR
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
Y1 - 2023
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
C2 - 37610134
AN - SCOPUS:85170089226
VL - 88
SP - 12853
EP - 12856
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 17
ER -