Oxidative trimerization of o-dialkoxybenzenes to hexaalkoxytriphenylenes: molybdenum(v) chloride as a novel reagent

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

Sandeep Kumar and M. Manickam


Abstract

Symmetrically substituted hexaalkoxytriphenylenes are obtained from o-dialkoxybenzenes by oxidative trimerization with MoCl5 in high yields; oxidative coupling of a 3,3′,4,4′-tetraalkoxybiphenyl and 1,2-dialkoxybenzenes yields unsymmetrically substituted derivatives of triphenylene and a direct coupling of a 3,3′,4,4′-tetraalkoxybiphenyl with alkoxyphenol produces the monofunctionalized triphenylenes.


References

  1. For a brief review of discotics, see S. Chandrasekhar, Liq. Cryst., 1993, 14, 3 Search PubMed See also S. Chandrasekhar and S. Kumar, Science Spectra, 1997, 8, 66 CrossRef CAS.
  2. N. Boden, R. Bissell, J. Clements and B. Movaghar, Liquid Crystals Today, 1996, 6, 1 Search PubMed.
  3. S. Kumar, P. Schuhmacher, P. Henderson, J. Rego and H. Ringsdorf, Mol. Cryst. Liq. Cryst., 1996, 288, 211 Search PubMed.
  4. (a) N. Boden, R. J. Bushby, A. N. Cammidge, S. Duckworth and G. Headdoc, J. Mater. Chem., 1997, 7, 601 RSC; (b) N. Boden, R. J. Bushby and A. N. Cammidge, Mol. Cryst. Liq. Cryst., 1995, 260, 307 Search PubMed; (c) N. Boden, R. J. Bushby and A. N. Cammidge, Liq. Cryst., 1995, 18, 673 CAS; (d) N. Boden, R. J. Bushby, A. N. Cammidge and G. Headdock, J. Mater. Chem., 1995, 5, 2275 RSC; (e) N. Boden, R. J. Bushby, A. N. Cammidge and G. Headdock, Synthesis, 1995, 31 CrossRef CAS; (f) N. Boden, R. J. Bushby and A. N. Cammidge, J. Chem. Soc., Chem. Commun., 1994, 465 RSC; (g) N. Boden, R. C. Borner, R. J. Bushby, A. N. Cammidge and M. V. Jesudason, Liq. Cryst., 1993, 15, 851 CAS.
  5. S. Kumar, Mol. Cryst. Liq. Cryst., 1996, 289, 247 Search PubMed; S. Kumar and M. Manickam, Mol. Cryst. Liq. Cryst., 1997, in the press Search PubMed.
  6. J. A. Rego, S. Kumar and H. Ringsdorf, Chem. Mater., 1996, 8, 1402 CrossRef CAS; J. A. Rego, S. Kumar, I. J. Dmochowski and H. Ringsdorf, Chem. Commun., 1996, 1031 RSC; P. Henderson, S. Kumar, J. A. Rego, H. Ringsdorf and P. Schuhmacher, J. Chem. Soc., Chem. Commun., 1995, 1059 RSC; F. Closs, L. Häussling, P. Henderson, H. Ringsdorf and P. Schuhmacher, J. Chem. Soc., Perkin Trans. 1, 1995, 829 RSC; P. Henderson, H. Ringsdorf and P. Schuhmacher, Liq. Cryst., 1995, 18, 191 CrossRef CAS.
  7. R. C. Borner and R. F. W. Jackson, J. Chem. Soc., Chem. Commun., 1994, 845 RSC.
  8. J. W. Goodby, M. Hird, K. J. Toyne and T. Watson, J. Chem. Soc., Chem. Commun., 1994, 1701 RSC.
  9. H. Naarmann, M. Hanack and R. Mattmer, Synthesis, 1994, 477 CrossRef CAS.
  10. (a) I. M. Matheson, O. C. Musgrave and C. J. Webster, Chem. Commun., 1965, 278 RSC; (b) O. C. Musgrave and C. J. Webster, J. Chem. Soc., 1971, 139 Search PubMed; (c) M. Piatelli, E. Fattorusso, R. A. Nicolaus and S. Magno, Tetrahedron, 1965, 21, 3229 CrossRef; (d) C. Destrade, M. C. Mondon and J. Malthete, J. Phys. Colloq., 1979, 40, C3 Search PubMed; (e) O. C. Musgrave, Chem. Rev., 1969, 69, 499 CrossRef CAS.
  11. K. Bechgaard and V. D. Parker, J. Am. Chem. Soc., 1972, 94, 4749 CrossRef CAS; V. Le Berre, L. Angely, N. Simonet-Gueguen and J. Simonet, J. Chem. Soc., Chem. Commun., 1987, 984 RSC; V. Le Berre, J. Simonet and P. Batail, J. Electroanal. Chem., 1984, 169, 325 CrossRef CAS; J. Chapuzet and J. Simonet, Tetrahedron, 1991, 47, 791 CrossRef CAS.
  12. H. Bengs, O. Karthaus, H. Ringsdorf, C. Baehr, M. Ebert and J. M. Wendorff, Liq. Cryst., 1991, 10, 161 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.