The synthesis of metal-free phthalocyanines from phthalonitriles with hexamethyldisilazane

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 7, 2004, Pages 1401-1404

  Uchida, Hitoshi ^a   Yoshiyama, Hideyuki ^a   Reddy, Paidi Yella ^a   Nakamura, Shuichi ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HEAT TREATMENT; NITRILE RESINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

PHTHALONITRILES; PTHALOCYANINES;

ORGANIC COMPOUNDS;

AMMONIUM SULFATE; HEXAMETHYLDISILAZANE; NAPHTHALENE DERIVATIVE; NAPHTHALOCYANINE; NITRILE; PHTHALOCYANINE DERIVATIVE; PHTHALONITRILE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEATING; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS; TECHNIQUE;

EID: 3342898496     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.1401     Document Type: Article

References (38)

1. a) F. H. Moser, "The Phthalocyanines: Properties," ed by A. L. Thomas, CRC Press, Boca Raton (1983), Vols. 1 and 2.
2. b) "Phthalocyanines: Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VCH, Weinheim (1989), Vol. 1; (1993), Vols 2 and 3; and (1996), Vol. 4.
3. b) "Phthalocyanines: Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VCH, Weinheim (1989), Vol. 1; (1993), Vols 2 and 3; and (1996), Vol. 4.
4. b) "Phthalocyanines: Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VCH, Weinheim (1989), Vol. 1; (1993), Vols 2 and 3; and (1996), Vol. 4.
5. c) A. L. Thomas, "The Phthalocyanines: Reserch and Applications," CRC Press, Boston (1990).
6. d) N. B. McKeown, "Phthalocyanine Materials, Synthesis, Structure and Function," Cambridge University Press, Cambridge (1998).
7. e) M. Hanack, H. Heckmann, and R. Policy, "Methods of Organic Chemistry," ed by E. Schaumann, Georg Thieme Verlag, Stuttgart (1998), Vol. E9d, p. 717-846.
8. f) G. Torre, C. G. Claessesns, and T. Torres, Eur. J. Org. Chem., 2000, 2821.
9. For example, see: a) V. F. Borodkin, J. Appl. Chem. USSR (Engl. Transl.), 31, 803 (1958).
10. b) B. I. Kharisov, L. M. Blanco, L. M. Torres-Martinez, and A. García-Luna, Ind. Eng. Chem. Res., 38, 2880 (1999).
11. a) H. Tomoda, S. Saito, S. Ogawa, and S. Shiraishi, Chem. Lett., 1980, 1277.
12. b) H. Tomoda, S. Saito, and S. Shiraishi, Chem. Lett., 1983, 313.
13. c) D. Wöhrle, G. Schnurpfeil, and G. Knothe, Dyes Pigm., 18, 91 (1992).
14. For example, see: a) P. J. Brach, S. J. Grammatica, O. A. Ossanna, and L. Weinberger, J. Heterocycl. Chem., 7, 1403 (1970).
15. b) N. Kobayshi and A. B. P. Laver, J. Am. Chem. Soc., 109, 7433 (1987).
16. K. Kitahara, T. Asano, S. Tokita, and H. Nishi, J. Heterocycl. Chem., 26, 1887 (1989).
17. a) C.-H. Lee and D. K. P. Ng, Tetrahedron Lett., 43, 4211 (2002).
18. On the other hand, Ce-phthalocyanine is formed in good yields under similar reaction conditions, see: b) L. G. Tomilova, E. V. Chernykh, T. B. Nikolaeva, V. V. Zelentsov, and E. A. Luk'yanets, J. Gen. Chem. USSR (Engl. Transl.), 54, 1494 (1984).
19. c) H. Isago and M. Shimoda, Chem. Lett., 1992, 147.
20. d) M. S. Haghighi, C. L. Teske, and H. Z. Homborg, Z. Anorg. Allg. Chem., 608, 73 (1992).
21. P. A. Barrett, C. E. Dent, and R. P. Linstead, J. Chem. Soc., 1936, 1719.
22. G. T. Byrne, R. P. Linstead, and A. R. Lowe, J. Chem. Soc., 1934, 1017.
23. a) A. W. Snow and N. L. Jarvis, J. Am. Chem. Soc., 106, 4706 (1984).
24. b) J. A. Tompson, K. Murata, D. C. Miller, J. L. Stanton, W. E. Broderick, B. M. Hoffman, and J. A. Ibers, Inorg. Chem., 32, 3546 (1993).
25. 2-PcS under high pressure, see: c) S. J. Edmondson, J. S. Hill, N. S. Isaacs, and C. H. Mitchell, J. Chem. Soc., Dalton Trans., 1990, 1115.
26. G. A. Timokhin, B. I. Kissin, and N. N. Faeshkina, J. Appl. Chem. USSR (Engl. Transl.), 42, 2187 (1969).
27. H. Uchida, H. Tanaka, H. Yoshiyama, P. Y. Reddy, S. Nakamura, and T. Toru, Synlett, 2002, 1649.
28. H. Uchida, P. Y. Reddy, S. Nakamura, and T. Toru, J. Org. Chem., 68, 8736 (2003).
29. H. Uchida, H. Yoshiyama, P. Y. Reddy, S. Nakamura, and T. Toru, Synlett, 2003, 2083.
30. 2-Pcs were also obtained by using DMAc in place of DMF.
31. a) C. C. Sweeley, R. Bentley, M. Makita, and W. W. Wells, J. Am. Chem. Soc., 85, 2497 (1963).
32. b) S. Torkelson and C. Ainsworth, Synthesis, 1976, 722.
33. c) R. S. Glass, J. Organomet. Chem., 61, 83 (1973).
34. G. Beaumont, C. Eaborn, and R. A. Jackson, J. Chem. Soc. B, 1970, 1624.
35. D. Wöhrle, M. Eskes, K. Shigehara, and A. Yamada, Synthesis, 1993, 194.
36. S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Luk'yanets, J. Gen. Chem. USSR (Engl. Transl.), 41, 2770 (1971).
37. V. M. Derkacheva and E. A. Luk'yanets, J. Gen. Chem. USSR (Engl. Transl.), 50, 1874 (1980).
38. S. A. Mikhalenko and E. A. Luk'yanets, J. Gen. Chem. USSR (Engl. Transl.), 39, 2495 (1969).