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Volumn , Issue 23, 2003, Pages 4533-4548

Further Studies on the Synthesis of meso-Tetraarylazuliporphyrins under Lindsey-Rothemund Reaction Conditions and Their Conversion into Benzocarbaporphyrins

Author keywords

Azulene; Azuliporphyrins; Porphyrinoids; Synthetic design

Indexed keywords

4 ANISALDEHYDE; 4 BROMOBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; 4 IODOBENZALDEHYDE; 4 METHYLBENZALDEHYDE; 4 NITROBENZALDEHYDE; ALDEHYDE; ANNULENE DERIVATIVE; AZULENE; AZULIPORPHYRIN; BENZALDEHYDE; BENZOCARBAPORPHYRIN; BENZYLAMINE; BORON TRIFLUORIDE; CARBAPORPHYRIN; HYDRAZINE; INDENE DERIVATIVE; PENTAFLUOROBENZALDEHYDE; PHENYL GROUP; PORPHYRIN DERIVATIVE; POTASSIUM HYDROXIDE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; TETRAPHENYLBENZOCARBAPORPHYRIN; THIOPHENOL; UNCLASSIFIED DRUG;

EID: 0345168783     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300530     Document Type: Article
Times cited : (56)

References (122)
  • 2
    • 0001004194 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego
    • T. D. Lash, in: The Porphyrin Handbook, Vol. 2 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 125-199.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 125-199
    • Lash, T.D.1
  • 4
    • 37049171709 scopus 로고
    • The first example of a nonaromatic "benziporphyrin" was reported in 1994: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 1356-1357; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246-1247. For related chemistry, see: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 229-230; Angew. Chem. Int. Ed. Engl. 1994, 33, 219-220. However, it is worth noting that non-aromatic examples of benzene and pyridine containing conjugated macrocycles related to the phthalocyanines have been known for over 50 years. See: R. P. Linstead, J. Chem. Soc., 1953, 2873-2884.
    • (1994) Angew Chem. , vol.106 , pp. 1356-1357
    • Berlin, K.1    Breitmaier, E.2
  • 5
    • 33748239902 scopus 로고
    • The first example of a nonaromatic "benziporphyrin" was reported in 1994: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 1356-1357; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246-1247. For related chemistry, see: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 229-230; Angew. Chem. Int. Ed. Engl. 1994, 33, 219-220. However, it is worth noting that non-aromatic examples of benzene and pyridine containing conjugated macrocycles related to the phthalocyanines have been known for over 50 years. See: R. P. Linstead, J. Chem. Soc., 1953, 2873-2884.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1246-1247
  • 6
    • 37049171709 scopus 로고
    • The first example of a nonaromatic "benziporphyrin" was reported in 1994: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 1356-1357; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246-1247. For related chemistry, see: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 229-230; Angew. Chem. Int. Ed. Engl. 1994, 33, 219-220. However, it is worth noting that non-aromatic examples of benzene and pyridine containing conjugated macrocycles related to the phthalocyanines have been known for over 50 years. See: R. P. Linstead, J. Chem. Soc., 1953, 2873-2884.
    • (1994) Angew Chem. , vol.106 , pp. 229-230
    • Berlin, K.1    Breitmaier, E.2
  • 7
    • 33748217175 scopus 로고
    • The first example of a nonaromatic "benziporphyrin" was reported in 1994: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 1356-1357; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246-1247. For related chemistry, see: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 229-230; Angew. Chem. Int. Ed. Engl. 1994, 33, 219-220. However, it is worth noting that non-aromatic examples of benzene and pyridine containing conjugated macrocycles related to the phthalocyanines have been known for over 50 years. See: R. P. Linstead, J. Chem. Soc., 1953, 2873-2884.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 219-220
  • 8
    • 37049171709 scopus 로고
    • The first example of a nonaromatic "benziporphyrin" was reported in 1994: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 1356-1357; Angew. Chem. Int. Ed. Engl. 1994, 33, 1246-1247. For related chemistry, see: K. Berlin, E. Breitmaier, Angew. Chem. 1994, 106, 229-230; Angew. Chem. Int. Ed. Engl. 1994, 33, 219-220. However, it is worth noting that non-aromatic examples of benzene and pyridine containing conjugated macrocycles related to the phthalocyanines have been known for over 50 years. See: R. P. Linstead, J. Chem. Soc., 1953, 2873-2884.
    • (1953) J Chem Soc. , pp. 2873-2884
    • Linstead, R.P.1
  • 9
    • 0000059175 scopus 로고
    • The first example of an aromatic carbaporphyrinoid system, "oxybenziporphyrin", was reported by our group in 1995. See: T. D. Lash, Angew. Chem. 1995, 107, 2703-2705; Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535.
    • (1995) Angew Chem. , vol.107 , pp. 2703-2705
    • Lash, T.D.1
  • 10
    • 33750614446 scopus 로고
    • The first example of an aromatic carbaporphyrinoid system, "oxybenziporphyrin", was reported by our group in 1995. See: T. D. Lash, Angew. Chem. 1995, 107, 2703-2705; Angew. Chem. Int. Ed. Engl. 1995, 34, 2533-2535.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2533-2535
  • 13
    • 0000327747 scopus 로고    scopus 로고
    • T. D. Lash, M. J. Hayes, Angew. Chem. 1997, 109, 868-870; Angew. Chem. Int. Ed. Engl. 1997, 36, 840-842.
    • (1997) Angew. Chem. , vol.109 , pp. 868-870
    • Lash, T.D.1    Hayes, M.J.2
  • 14
    • 0030916482 scopus 로고    scopus 로고
    • T. D. Lash, M. J. Hayes, Angew. Chem. 1997, 109, 868-870; Angew. Chem. Int. Ed. Engl. 1997, 36, 840-842.
    • (1997) Angew Chem. Int. Ed. Engl. , vol.36 , pp. 840-842
  • 15
    • 0000270904 scopus 로고    scopus 로고
    • T. D. Lash, S. T. Chaney, Angew. Chem. 1997, 109, 867-868; Angew. Chem. Int. Ed. Engl. 1997, 36, 839-840.
    • (1997) Angew. Chem. , vol.109 , pp. 867-868
    • Lash, T.D.1    Chaney, S.T.2
  • 16
    • 0030905554 scopus 로고    scopus 로고
    • T. D. Lash, S. T. Chaney, Angew. Chem. 1997, 109, 867-868; Angew. Chem. Int. Ed. Engl. 1997, 36, 839-840.
    • (1997) Angew Chem. Int. Ed. Engl. , vol.36 , pp. 839-840
  • 18
    • 0011246374 scopus 로고    scopus 로고
    • K. Berlin, Angew. Chem. 1996, 108, 1955-1957; Angew. Chem. Int. Ed. Engl. 1996, 35, 1820-1822.
    • (1996) Angew. Chem. , vol.108 , pp. 1955-1957
    • Berlin, K.1
  • 19
    • 0030485295 scopus 로고    scopus 로고
    • K. Berlin, Angew. Chem. 1996, 108, 1955-1957; Angew. Chem. Int. Ed. Engl. 1996, 35, 1820-1822.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1820-1822
  • 32
    • 0037090891 scopus 로고    scopus 로고
    • S. R. Graham, D. A. Colby, T. D. Lash, Angew. Chem. 2002, 114, 1429-1432; Angew. Chem. Int. Ed. 2002, 41, 1371-1374.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1371-1374
  • 50
    • 0031002017 scopus 로고    scopus 로고
    • S. Will, J. Lex, E. Vogel, H. Schmickler, J. P. Gisselbrecht, C. Haubtmann, M. Bernard, M. Gross, Angew. Chem. 1997, 109, 367-371; Angew. Chem. Int. Ed. Engl. 1997, 36, 357-361.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 357-361
  • 53
    • 0034680594 scopus 로고    scopus 로고
    • Z. Gross, G. Golubkov, L. Simkhovich, Angew. Chem. 2000, 112, 4211-4213, Angew. Chem. Int. Ed. 2000, 39, 4045-4047.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4045-4047
  • 57
    • 0000303285 scopus 로고    scopus 로고
    • K. M. Kadish, K. M. Smith, R. Guilard, Eds.; Academic Press: San Diego
    • [a] R. K. Pandey, G. Zheng, in: The Porphyrin Handbook, K. M. Kadish, K. M. Smith, R. Guilard, Eds.; Academic Press: San Diego, 2000, Vol. 6, pp. 157-230.
    • (2000) The Porphyrin Handbook , vol.6 , pp. 157-230
    • Pandey, R.K.1    Zheng, G.2
  • 62
    • 0001938751 scopus 로고    scopus 로고
    • (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego
    • J. S. Lindsey, in: The Porphyrin Handbook, Vol. 1 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 45-118.
    • (2000) The Porphyrin Handbook , vol.1 , pp. 45-118
    • Lindsey, J.S.1
  • 70
    • 0002447763 scopus 로고
    • (Ed. D. Dolphin), Academic Press, New York
    • [e] J. B. Kim, A. D. Adler, F. R. Longo, in: The Porphyrins (Ed. D. Dolphin), Academic Press, New York, 1978, vol. 1, pp. 85-100.
    • (1978) The Porphyrins , vol.1 , pp. 85-100
    • Kim, J.B.1    Adler, A.D.2    Longo, F.R.3
  • 76
    • 33748244301 scopus 로고
    • [b] P. J. Chmielewski, L. Latos-Grazynski, K. Rachlewicz, T. Glowiak, Angew. Chem. 1994, 106, 805-807; Angew. Chem. Int. Ed. Engl. 1994, 33, 779-781.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 779-781
  • 82
    • 0344756408 scopus 로고    scopus 로고
    • Kyoto, Japan June 30-July 5
    • Further details of these studies were reported at the following meetings: [58a] 2nd International Conference on Porphyrins and Phthalocyanines (ICPP-2), Kyoto, Japan, June 30-July 5, 2002 (D. A. Colby, T. D. Lash, Book of Abstracts, Abstract No. P-247).
    • (2002) 2nd International Conference on Porphyrins and Phthalocyanines (ICPP-2)
  • 83
    • 0004329798 scopus 로고    scopus 로고
    • Abstract No P-247
    • Further details of these studies were reported at the following meetings: [58a] 2nd International Conference on Porphyrins and Phthalocyanines (ICPP-2), Kyoto, Japan, June 30-July 5, 2002 (D. A. Colby, T. D. Lash, Book of Abstracts, Abstract No. P-247).
    • Book of Abstracts
    • Colby, D.A.1    Lash, T.D.2
  • 84
    • 0011946220 scopus 로고    scopus 로고
    • Boston, Massachusetts, U. S. A., August 18-22
    • [b] 224th National Meeting of the American Chemical Society, Boston, Massachusetts, U. S. A., August 18-22, 2002 (D. A. Colby, T. D. Lash, Book of Abstracts, CHED 218).
    • (2002) 224th National Meeting of the American Chemical Society
  • 85
    • 0004329798 scopus 로고    scopus 로고
    • CHED 218
    • [b] 224th National Meeting of the American Chemical Society, Boston, Massachusetts, U. S. A., August 18-22, 2002 (D. A. Colby, T. D. Lash, Book of Abstracts, CHED 218).
    • Book of Abstracts
    • Colby, D.A.1    Lash, T.D.2
  • 86
    • 0013057279 scopus 로고    scopus 로고
    • New Orleans, Louisiana U. S. A., March 23-27
    • [c] 225th National Meeting of the American Chemical Society, New Orleans, Louisiana, U. S. A., March 23-27, 2003 (D. A. Colby, T. D. Lash, Book of Abstracts, ORGN 330).
    • (2003) 225th National Meeting of the American Chemical Society
  • 87
    • 0345186672 scopus 로고    scopus 로고
    • Book of Abstracts, ORGN 330
    • [c] 225th National Meeting of the American Chemical Society, New Orleans, Louisiana, U. S. A., March 23-27, 2003 (D. A. Colby, T. D. Lash, Book of Abstracts, ORGN 330).
    • Colby, D.A.1    Lash, T.D.2
  • 90
    • 0011290191 scopus 로고
    • T. D. Lash, B. H. Novak, Angew. Chem. 1995, 107, 723-725; Angew. Chem. Int. Ed. Engl. 1995, 34, 683-685.
    • (1995) Angew. Chem. , vol.107 , pp. 723-725
    • Lash, T.D.1    Novak, B.H.2
  • 91
    • 33748220009 scopus 로고
    • T. D. Lash, B. H. Novak, Angew. Chem. 1995, 107, 723-725; Angew. Chem. Int. Ed. Engl. 1995, 34, 683-685.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 683-685
  • 100
    • 0345186669 scopus 로고    scopus 로고
    • unpublished work
    • In our studies on calixazulenes, we have found azulene carbinols to be highly reactive compounds which may afford unexpected condensation products (D. A. Colby, T. D. Lash, unpublished work). See also ref. [59b].
    • Colby, D.A.1    Lash, T.D.2
  • 107
    • 0033577883 scopus 로고    scopus 로고
    • Z. Gross, N. Galili, I. Saltsman, Angew. Chem. 1999, 111, 1530-1533; Angew. Chem. Int. Ed. 1999, 38, 1427-1430.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1427-1430
  • 109
    • 0344324232 scopus 로고    scopus 로고
    • note
    • Insufficient material was obtained for 6h to conduct oxidative ring contraction studies. However, a fraction of mixed carbaporphyrins obtained as a by-product in the synthesis of 6h gave a Soret band at 441 nm, which represents a significantly lower wavelength than is observed for tetraphenylbenzocarbaporphyrins 19a-c.
  • 114
    • 0344756407 scopus 로고    scopus 로고
    • note
    • The data reported here for 6a and 19a-c represents additional information, and more complete physical, spectroscopic, and mass spectrometric characterizations for these compounds can be found in ref. [3].
  • 115
    • 0242272061 scopus 로고    scopus 로고
    • Bruker Advanced X-ray Solutions: Madison, Wisconsin
    • Bruker SMART 1000 CCD software package; Bruker Advanced X-ray Solutions: Madison, Wisconsin, 1999.
    • (1999) Bruker Smart 1000 CCD Software Package
  • 122
    • 0004150157 scopus 로고    scopus 로고
    • Programs for X-ray Structure Determination; University of Göttingen: Göttingen, Germany
    • G. M. Sheldrick, SHELXS-97; 97-2 ed., Programs for X-ray Structure Determination; University of Göttingen: Göttingen, Germany, 1997.
    • (1997) SHELXS-97; 97-2 Ed.
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.