Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF)

Olivier J. Dautel (1) , Marc Fourmigué (1) , Jan Larsen (1)

1 IMN - Institut des Matériaux Jean Rouxel

The SO2Cl2 chlorination of 5,6-dihydro-1,3-dithiolo[4,5-b]- [1,4]dithiine-2-one affords the corresponding mono- and trans-di-chloro derivatives which eliminate HCl upon treatment with KF/18-crown-6 or LiBr/HMPA, offering an easy route to the unsaturated vinylenedithiotetrathiafulvalene (VDT-TTF).

Domaines: Chimie organique; Matériaux; Cristallographie

Olivier J. Dautel, Marc Fourmigué, Jan Larsen. Electrophilic halogenation of thioethers: 5-chloro- and 5,6-dichloro-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiine-2-one and an efficient synthesis of vinylenedithiotetrathiafulvalene (VDT-TTF). Chemical Communications, 2000, 13, pp.1117-1118. ⟨10.1039/b001996h⟩. ⟨hal-00178011⟩