A Facile Approach to New Vinylogous Tetrathiafulvalene (TTF) Derivatives: 2,3-Bis(1,3-dithiole-2-ylidene)succinonitriles

Abstract

A new approach to vinylogous TTF derivatives 5 via an alkyne-coupling reaction is reported. Their fundamental redox behavior has been studied. A proposed reaction mechanism, which accounts for the formation of compounds 5 is discussed.

cycloadditions - substituent effects - sulfur - synthesis - vinylogous tetrathiafulvalene

References

<A NAME="RT16004SS-1A">1a</A> Moore A. Bryce MR. Tetrahedron Lett.  1992,  55:  1373 

<A NAME="RT16004SS-1B">1b</A> Lorcy D. Carlier R. Robert A. Tallec A. Magueres PL. Ouahab L. J. Org. Chem.  1995,  60:  2443 

<A NAME="RT16004SS-1C">1c</A> Hascoat P. Lorcy D. Robert A. Carlier R. Tallec A. Boubekeur K. Batail P. J. Org. Chem.  1997,  62:  6086 

<A NAME="RT16004SS-1D">1d</A> Yu LH. Zhu DB. Chem. Commun.  1997,  787 

<A NAME="RT16004SS-1E">1e</A> Yamashita Y. Tomura M. Badruz Zaman M. Imaeda K. Chem. Commun.  1998,  1657 

<A NAME="RT16004SS-1F">1f</A> Bellec N. Boubekeur K. Carlier R. Hapiot P. Lorcy D. Tallec A. J. Phys. Chem. A  2000,  104:  9750 

<A NAME="RT16004SS-1G">1g</A> Frere P. Boubekeur K. Jubault M. Batail P. Gorgue A. Eur. J. Org. Chem.  2001,  3741 

<A NAME="RT16004SS-2A">2a</A> Bryce MR. Moore AJ. Tanner BK. Whitehead R. Clegg W. Chem. Mater.  1996,  8:  1182 

<A NAME="RT16004SS-2B">2b</A> Yamashita Y. Tomura M. Tanaka S. Imaeda K. Synth. Met.  1999,  102:  1730 

<A NAME="RT16004SS-2C">2c</A> Misaki Y. Natsume Y. Takahashi K. Fueno H. Tanaka K. Synth. Met.  2003,  135-136:  671 

<A NAME="RT16004SS-2D">2d</A> Guerro M. Carlier R. Boubekeur K. Lorcy D. Hapiot P. J. Am. Chem. Soc.  2003,  125:  3159 

<A NAME="RT16004SS-3A">3a</A> Moore AJ. Bryce MR. Ando DJ. Hursthouse MB. J. Chem. Soc., Chem. Commun.  1991,  320 

<A NAME="RT16004SS-3B">3b</A> Bryce MR. Coffin MA. Clegg W. J. Org. Chem.  1992,  57:  1696 

<A NAME="RT16004SS-4">4</A> Schoberl U. Salbeck J. Daub J. Adv. Mater.  1992,  4:  41 

<A NAME="RT16004SS-5A">5a</A> Engler EM. Patel VV. Tetrahedron Lett.  1981,  22:  2035 

<A NAME="RT16004SS-5B">5b</A> Papavassiliou GC. Mousdis GA. Yiannopoulos SY. Kakoussis VC. Zambounis JS. Synth. Met.  1988,  27:  B373 

<A NAME="RT16004SS-5C">5c</A> Cooke G. Powell AK. Heath SL. Synthesis  1995,  1411 

<A NAME="RT16004SS-5D">5d</A> Zhong ZJ. You XZ. Yu KB. Acta Crystallogr., Sect. C.  1996,  52:  449 

<A NAME="RT16004SS-5E">5e</A> Cooke G. Synth. Commun.  1996,  26:  2917 

<A NAME="RT16004SS-6A">6a</A> Engler EM. Scott BA. Etemad S. Penney T. Patel VV. J. Am. Chem. Soc.  1977,  99:  5909 

<A NAME="RT16004SS-6B">6b</A> Jia CY. Zhang DQ. Guo XF. Wan SH. Xu W. Zhu DB. Synthesis  2002,  2177 

<A NAME="RT16004SS-7">7</A>

Slow evaporation of the solution of 5b in CH₂Cl₂ gave single crystals suitable for X-ray diffraction measurement. Crystal data for compound 5b: C₁₄H₁₂N₂S₈, MW = 464, monoclinic, C ₂, a = 16.527 (2), b = 5.2211 (6), c = 12.897 (2) Å; β = 118.955 (13)°, V = 973.8 (2) ų, T = 153 (2) K, Z = 2, D_c = 1.585 g·cm^-3, µ = 0.917 mm^-1, λ = 0.71073 Å, F(000) = 476, independent reflections (R _int = 0.1017), 3870 reflections collected; refinement method, full-matrix least-squares refinement on F²; goodness-of-fit on F ² = 0.761; Final R indices [I > 2σ(I)] R1 = 0.048, wR2 = 0.118.

<A NAME="RT16004SS-8">8</A> Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 

<A NAME="RT16004SS-9A">9a</A> Hopf H. Kreutzer M. Jones PG. Angew. Chem., Int. Ed. Engl.  1991,  30:  1127 

<A NAME="RT16004SS-9B">9b</A> Schermann G. Vostrowsky O. Hirsch A. Eur. J. Org. Chem.  1999,  2491 

<A NAME="RT16004SS-10">10</A> Ciganek E. Krespan CG. J. Org. Chem.  1968,  33:  541 

<A NAME="RT16004SS-11A">11a</A> Demko ZP. Sharpless KB. J. Org. Chem.  2001,  66:  7945 

<A NAME="RT16004SS-11B">11b</A> Vagin S. Barthel M. Dini D. Hanack M. Inorg. Chem.  2003,  42:  2683