Tetramethyltetraselenafulvalene is the organoselenium compound with the chemical formula ((CH3)2C2Se2C)2. It is one of the heterofulvalenes.
Structure TMTSF is a planar molecule with C2v symmetry. It is structurally analogous to tetramethyltetrathiafulvalene (TMTTF). This structure is suitable for the role of TMTSF as an electron donor and the formation of some charge-transfer salts. A notable family of derivatives are the Bechgaard salts, e.g., (TMTSF)2PF6, the first organic superconductor.
Synthesis TMTSF is prepared from 3-chloro-2-butanone via a triselenocarbonate. Diethylselenocarbamate is a source of Se.
CH3C(O)CHClCH3 + (CH3CH2)2NCSe−2 → (CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + Cl− (CH3CH2)2NC(Se)SeCHC(O)(CH3)2 + 2H+ → (CH3CH2)2N=CSe2C2(CH3)+2 + H2O (CH3CH2)2N=CSe2C2(CH3)+2 + SeH− → Se=CSe2C2(CH3)2 + (CH3CH2)2NH 2 Se=CSe2C2(CH3)2 + 2 P(OCH3)3 → (CH3)2C2Se2C=CSe2C2(CH3)2 + 2 SeP(OCH3)3
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