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Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones.

ABSTRACT: Enantiopure (R,R) and (S,S)-dimethyl-bis(ethylenedithio)tetrathiafulvalene monosulfones have been synthesized by the aerial oxidation of the chiral dithiolates generated from the propionitrile-protected precursors. Both enantiomers crystallize in the orthorhombic chiral space group P212121. They show a boat-type conformation of the TTF moiety, a rather rigid dithiin sulfone ring and the methyl groups in a bisequatorial conformation. Cyclic voltammetry measurements indicate fully reversible oxidation in radical cation and dication species.

SUBMITTER: Pop F

PROVIDER: S-EPMC4505188 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones.

Pop Flavia F Avarvari Narcis N

Beilstein journal of organic chemistry 20150702

Enantiopure (R,R) and (S,S)-dimethyl-bis(ethylenedithio)tetrathiafulvalene monosulfones have been synthesized by the aerial oxidation of the chiral dithiolates generated from the propionitrile-protected precursors. Both enantiomers crystallize in the orthorhombic chiral space group P212121. They show a boat-type conformation of the TTF moiety, a rather rigid dithiin sulfone ring and the methyl groups in a bisequatorial conformation. Cyclic voltammetry measurements indicate fully reversible oxida ...[more]

PMID: 26199666

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