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Beilstein J. Org. Chem. 2015, 11, 403–415, doi:10.3762/bjoc.11.46
Graphical Abstract
Figure 1: Chemical structure of the TTF analogues and TCNQ.
Figure 2: Oxidation states of TTF.
Figure 3: 1,4-Dithiin and thiophene fused TTF analogues from 1,8-diketone.
Scheme 1: Reaction mechanism of fused 1,4-dithiin and thiophene ring systems.
Scheme 2: Reaction conditions (i) LR, toluene, reflux, overnight; (ii) P4S10, toluene, reflux, 3 h.
Scheme 3: Proposed mechanism for side products.
Scheme 4: Reaction conditions (i) Hg(OAc)2, AcOH/CHCl3, rt, 1h; (ii) (EtO)3P, N2, 3 h, 110 °C.
Scheme 5: Reaction conditions (i) iPr2NEt, MEMCl, THF, rt, 12 h; (ii) LiAlH4, dry ether, rt, 24 h; (iii) tosy...
Scheme 6: Reagents and conditions (i) P4S10, toluene, reflux, dark, 3 h; (ii) P4S10, toluene, reflux, 3 h; (i...
Scheme 7: Reagents and conditions (i) Hg(OAc)2–AcOH, CHCl3, 3 h, rt; (ii) (EtO)3P, 110 °C, N2, 2 h.
Scheme 8: Charge transfer complex of 5,5',6,6'-tetraphenyl-2,2'-bi([1,3]dithiolo[4,5-b][1,4]dithiinylidene) 52...
Scheme 9: Reaction conditions (i) (EtO)3P, 110 °C, N2, 2 h.
Scheme 10: Reaction conditions (i) EtOH, reflux, overnight; (ii) diisopropylethylamine in CH2Cl2, room tempera...
Scheme 11: Reaction and conditions (i) P4S10, NaHCO3, toluene, reflux, 3 h; (ii) P4S10, p-TSA, toluene, reflux...