View PDF Version
 
DOI: 10.1039/A605468D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 709-714

Synthesis of 1,4-di(n-pyridyl)buta-1,3-diyne and formation of charge-transfer complexes. X-Ray structure of 1,4-di(3-pyridyl)buta-1,3-diyne

(Note: The full text of this document is currently only available in the PDF Version )

J. Gonzalo Rodríguez, Rosa Martín-Villamil, Felix H. Cano and Isabel Fonseca

Abstract

Ethynylpyridines have been satisfactorily prepared by two different routes: (a) the Wittig reaction between chloromethylene(triphenyl)phosphine ylide and a pyridinecarbaldehyde, followed by elimination of hydrogen chloride; (b) from the 2-methyl-4-(n-pyridyl)but-3-yn-2-ol intermediate, by elimination of acetone. 1,4-Di(n-pyridyl)buta-1,3-diynes are obtained by oxidative dimerization in good yield. An X-ray structure of the 3-substituted dimer is reported. Mono- and di-methyl salts of the 3-substituted diyne have been obtained and the charge-transfer complexes with tetramethyl-p-phenylenediamine (TMPD) are formed.

References

  1. Polydiacetylenes, ed. D. Bloor and R. R. Chance, NATO ASI series E, No. 102, Matinus Nijkoff, Boston, 1985; A. E. Stiegman, E. Graham, K. J. Perry, R. Khundkard, L. T. Cheng and J. W. Perry, J. Am. Chem. Soc., 1991, 113, 1658 Search PubMed and references cited therein.
  2. G. Wegner, Z. Naturforsch., B: Anorg. Chem., Org. Chem., 1969, 24, 824 CAS.
  3. G. M. Carter, Y. J. Chen, M. F. Rubner, D. J. Sandman, M. K. Thakur and S. K. Tripathy, in Nonlinear Optical Properties of Organic Molecules and Crystals, ed. D. S. Chemla and J. Zyss, Academic Press, New York, 1987, vol. 2, p. 85 Search PubMed.
  4. G. Wegner, J. Polym. Sci., Part B: Polym. Lett., 1971, 9, 133 CrossRef CAS.
  5. Y. Ozcayir, J. Asrar and A. Blumstein, Mol. Cryst. Liq. Cryst., 1984, 110, 1424.
  6. G. H. Milburn, A. R. Wernick, J. Tsibouklis, E. Bolton, G. Thomson and A. Shand, Polymer, 1989, 30, 1004 CrossRef CAS.
  7. J. P. Ferraris, D. O. Cowan, V. Walatka and J. Perlstein, J. Am. Chem. Soc., 1973, 95, 948 CrossRef CAS.
  8. G. Köbrig, H. Trapp, K. Flory and W. Drischel, Chem. Ber., 1966, 99, 689.
  9. D. E. Ames, D. Bull and C. Takundwa, Synth. Commun., 1981, 364 CAS.
  10. L. Brandsma, Studies in Organic Chemistry: Preparative Acetylenic Chemistry, Elsevier Science Publishers B. V., Amsterdam, 1988, vol. 34, p. 220 Search PubMed.
  11. J. G. Rodríguez, S. Ramos, R. Martín-Villamil, I. Fonseca and A. Albert, J. Chem. Soc., Perkin Trans. 1, 1996, 541 RSC.
  12. G. M. J. Schmidt, Reactivity of the Photoexcited Organic Molecule, Wiley, New York, 1967, p. 227 Search PubMed.
  13. S. D. L'vova, Y. P. Koslov and U. I. Gunar, Zh. Obshch. Khim., 1977, 47, 1251 CAS.
  14. A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, Dipartimento Geomineralogico, University of Bari; M. Burla and G. Polidori, Dipartimento Scienze della Terra, University of Perugia; M. Camalli, SIR92, Ist Strutt. Chimica, CNR, Monterrotondo Stazione, Roma, 1992.
  15. J. M. Stewart, F. A. Kundell and J. C. Badwin, The XRAY80 System, Computer Science Center, University of Maryland, College Park, MD, 1980.
  16. M. Martinez-Ripoll and F. H. Cano, PESOS, A Computer Program for the Automatic Treatment of Weighting Schemes, Instituto Rocasolano, CSIC, Madrid, 1975.
  17. International Tables for X-RAY Crystallography, Kynoch Press, Birmingham, 1974, vol. 4.
  18. M. Nardelli, Comput. Chem., 1983, 7, 95 CrossRef CAS.
  19. U. Fritzsche and S. Hunig, Tetrahedron Lett., 1972, 4831 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.