Synthesis and properties of novel bis(1,3-benzodithiolium)-type dications containing a biaryl unit: new redox systems undergoing reversible structural changes by electron transfer

Heterocycles

Volumn 69, Issue 1, 2006, Pages 365-375

  Ohta, Akira ^a   Ueki, Chihiro ^a   Uchiyama, Yuzuru ^a   Fujimori, Kunihide ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947276686     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-S(O)45     Document Type: Article

References (18)

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10. Wizinger-Aust R. Q. Rep. Sulfur Chem. 5 (1970) 191
11. We used p-toluenesulfonic acid as an acid catalyst instead of HCI gas. When the experimental condition described in this literature was applied to the present synthesis, a complex mixture was formed. Nakayama J., Ueda K., and Hoshino M. Synthesis 770 (1977)
12. Bacon R.G.R., and Lindsay W.S. J. Chem. Soc. (1958) 1375
13. Wynberg H., Sinnige H.J.M., and Sinnige H.J.M. Rec. Trav. Chim. Pays-Bas 88 (1969) 1244
14. 13C-NMR spectrum of the biphenyl derivative (6c) shows six kinds of aromatic carbon signals of the spiro-1,3-benzodithiole moiety, suggesting that the inversion of the central six-membered ring is sufficiently slow under the measurement time scale.
15. 2+) at -0.20 and -0.18 (weak) V, respectively.When the potential sweep was reversed after the second reduction peak, any other oxidation peaks additional to the oxidation of 6 were observed in reverse scan. Reasonable assignment of these second reduction process is unclear at present.
16. 2+) revealed by the X-Ray analyses may be caused by various effects such as conjugation interactions between the heteroaromatic rings, intramolecular steric interactions, crystal packing effects, and the influence of the counterions.
17. Sheldrick G.M. Acta Crystallogr. A46 (1990) 467
18. Sheldrick G.M. SHELX93. A program for the Refinement of Crystal Structure (1993), Universität, Göttingen