The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

Canadian Journal of Chemistry

Volumn 74, Issue 3, 1996, Pages 307-318

  Leznoff, Clifford C ^a   Drew, David M ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

1,11,15,25 tetrasubstituted phthalocyanines; Bisphthalonitriles; Nucleophilic aromatic substitution; Phthalonitriles

Indexed keywords

ALCOHOLS; CONDENSATION REACTIONS; DERIVATIVES; LITHIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BISPHTHALONITRILES; DILUTION; GEM DIMETHYL EFFECT; ISOMERS; LITHIUM OCTOXIDE; MACROCYCLIZATIONS; NUCLEOPHILIC AROMATIC SUBSTITUTION; OCTANOL; TETRASUBSTITUTED PHTHALOCYANINES;

AROMATIC COMPOUNDS;

EID: 0030105904     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-035     Document Type: Article

References (38)

1. C.C. Leznoff. In Phthalocyanines; properties and applications. Vol. 1. Edited by C.C. Leznoff and A.B.P. Lever. VCH, New York. 1989.
2. S. Greenberg, A.B.P. Lever, and C.C. Leznoff. Can. J. Chem. 66, 1059 (1988).
3. S. Gaspard and Ph. Maillard. Tetrahedron, 43, 1083 (1987).
4. C.C. Leznoff, M. Hu, C.R. McArthur, Y. Qin, and J.E. van Lier. Can. J. Chem. 72, 1990 (1994).
5. M. Hanack, G. Renz, J. Strähle, and S. Schmid. J. Org. Chem. 66, 3501 (1991).
6. D.M. Drew and C.C. Leznoff. Synlett, 623 (1994).
7. M. Hanack, G. Schmid, and M. Sommerauer. Angew Chem. Int. Ed. Engl. 32, 1422 (1993).
8. V.M. Derkacheva, S.S. Iodko, O.L. Kaliya, and E.A. Luk'yanets. Zh. Obshch. Khim. 51, 2319 (1981).
9. C.C. Leznoff, D.S. Terekhov, C.R. McArthur, S. Vigh, and J. Li. Can. J. Chem. 73, 435 (1995); R.D. George and A.W. Snow. J. Heterocycl. Chem. 32, 495 (1995); D.M. Drew. Ph.D. Thesis, York University, 1995. pp. 50-52.
10. C.C. Leznoff, D.S. Terekhov, C.R. McArthur, S. Vigh, and J. Li. Can. J. Chem. 73, 435 (1995); R.D. George and A.W. Snow. J. Heterocycl. Chem. 32, 495 (1995); D.M. Drew. Ph.D. Thesis, York University, 1995. pp. 50-52.
11. C.C. Leznoff, D.S. Terekhov, C.R. McArthur, S. Vigh, and J. Li. Can. J. Chem. 73, 435 (1995); R.D. George and A.W. Snow. J. Heterocycl. Chem. 32, 495 (1995); D.M. Drew. Ph.D. Thesis, York University, 1995. pp. 50-52.
12. V.A. Ustinov, V.V. Plakhtinskii, G.X. Mironov, and N.S. Ryabukhina. Zh. Org. Khim. 15, 1775 (1979).
13. P.J. Brach, S.J. Grammatica, O.A. Ossanna, and L. Weinberger, J. Heterocycl. Chem. 7, 1403 (1970); G. Pawlowski and M. Hanack. Synthesis, 287 (1980).
14. P.J. Brach, S.J. Grammatica, O.A. Ossanna, and L. Weinberger, J. Heterocycl. Chem. 7, 1403 (1970); G. Pawlowski and M. Hanack. Synthesis, 287 (1980).
15. C.C. Leznoff, S.M. Marcuccio, S. Greenberg, A.B.P. Lever, and K.B. Tomer. Can. J. Chem. 63, 623 (1985).
16. A.W. Dox and E.G. Jones. J. Am. Chem. Soc. 50, 2033 (1928).
17. W.M. Stanley, M.S. Jay, and R. Adams. J. Am. Chem. Soc. 51, 1261 (1929).
18. J.F.W. McOmie and W.L. Watts. Chem. Ind. 1658 (1963).
19. J.F.W. McOmie, M.L. Watts, and D.E. West. Tetrahedron, 24, 2289 (1968).
20. I. Rosenthal, E. Ben-Hur, S. Greenberg, A. Concepcion-Lam, D.M. Drew, and C.C. Leznoff. Photochem. Photobiol. 46, 959 (1987).
21. M.V . Bhatt and J.R. Babu. Tetrahedron Lett. 25, 3497 (1984); S. Anderson. Synthesis, 3497 (1984).
22. M.V . Bhatt and J.R. Babu. Tetrahedron Lett. 25, 3497 (1984); S. Anderson. Synthesis, 3497 (1984).
23. L.F. Fieser and M. Fieser. Reagents for organic synthesis. Vol. I. J. Wiley and Sons, Inc., New York, 1967, p. 581.
24. G. Hummel and K. Ruhl. German Pat. 922,648 (1955); Chem. Abstr. 52, 1219e (1958).
25. R. Kreher and W. Gerhardt. Liebigs Ann. Chem. 240 (1981).
26. M.A. McCall, J.R. Caldwell, H.G. Moore, and H.M. Beard. J. Macromol. Sci. Chem. 5, 911 (1969).
27. J.M. Timki, S.S. Moore, D.M. Walba, P.C. Hiberty, and D.J. Cram. J. Am. Chem. Soc. 99, 4207 (1977).
28. R.M. Beesley, C.K. Ingold, and J.F. Thorpe. J. Chem. Soc. 107, 1080 (1915).
29. C.K. Ingold, J. Chem. Soc. 119, 305 (1921); C.K. Ingold. J. Chem. Soc. 119, 951 (1921).
30. C.K. Ingold, J. Chem. Soc. 119, 305 (1921); C.K. Ingold. J. Chem. Soc. 119, 951 (1921).
31. N.L. Allinger and V. Zalkow. J. Org. Chem. 25, 701 (1960).
32. B.L. Shaw. J. Am. Chem. Soc. 97, 3856 (1975).
33. P.J. Duggan and P.F. Gordon. Eur. Pat. Appl. Ep. 155 780 (1985); Chem. Abstr. 105, 72642 (1987).
34. M.J. Cook, A.J. Dunn, S.D. Howe, A.J. Thomson, and K.J. Harrison, J. Chem. Soc. Perkin Trans. 1, 2453 (1988).
35. N. Kobayashi, T. Ashida, and T. Osa. Chem. Lett. 2031 (1992).
36. N. Kobayashi, Y. Kobayashi, and T. Osa. J. Am. Chem. Soc. 115, 10994 (1993).
37. T.R. Janson and J.J. Katz. In The porphyrins: physical chemistry, Part B. Edited by D. Dolphin. Academic Press, New York. 1979, p. 1.
38. W.O. Siegl. J. Heterocycl. Chem. 18, 1613 (1981).