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Volumn , Issue 21, 2007, Pages 3468-3475

A facile and reliable method for the synthesis of tetrabenzoporphyrin from 4,7-dihydroisoindole

Author keywords

extended porphyrins; Dipyrromethanes; Nitrogen heterocycles; Porphyrinoids; Tetrabenzoporphyrins

Indexed keywords


EID: 34447571836     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700014     Document Type: Article
Times cited : (55)

References (98)
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    • Eds, K. M. Kadish, K. M. Smith, R. Guilard, Academic Press, New York
    • T. D. Lash in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 2000, vol. 2, pp. 1-54.
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    • and references cited therein. 2013
    • b) S. H. Lee, K. M. Smith, Tetrahedron Lett. 2005, 46, 2009-2013; and references cited therein.
    • (2005) Tetrahedron Lett , vol.46
    • Lee, S.H.1    Smith, K.M.2
  • 66
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    • In a forthcoming paper we shall report an essential update on the aromatization protocol in the former approach to TBP that is based on tetrahydroisoindole, which however does not completely eliminate the main problem - losses of porphyrin owing to overoxidation and other side reactions.
    • In a forthcoming paper we shall report an essential update on the aromatization protocol in the former approach to TBP that is based on tetrahydroisoindole, which however does not completely eliminate the main problem - losses of porphyrin owing to overoxidation and other side reactions.
  • 67
    • 34447510588 scopus 로고    scopus 로고
    • Although a poor choice, isomeric 6,7-dihydroisoindole should also be considered as the conjugated and very electron-rich double bond in this compound can be an alternative reaction center in the electrophilic reactions; thus, many side reactions are anticipated
    • Although a poor choice, isomeric 6,7-dihydroisoindole should also be considered as the conjugated and very electron-rich double bond in this compound can be an alternative reaction center in the electrophilic reactions; thus, many side reactions are anticipated.
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    • 34447501398 scopus 로고    scopus 로고
    • This material was partially presented at the 4th International Conference on Porphyrins and Phthalocyanines, Rome, 2-7 July, 2006: M. A. Filatov, A. V. Cheprakov, J. Porph. Phthalocyanines 2006, 10, 630
    • This material was partially presented at the 4th International Conference on Porphyrins and Phthalocyanines, Rome, 2-7 July, 2006: M. A. Filatov, A. V. Cheprakov, J. Porph. Phthalocyanines 2006, 10, 630.
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    • a) T. G. Back, Tetrahedron 2001, 57, 5263-5301;
    • (2001) Tetrahedron , vol.57 , pp. 5263-5301
    • Back, T.G.1
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    • useful modification of the more convenient unsaturated sulfones in place of nitro olefins was first developed in: b Y. Abel, E. Haake, G. Haake, W. Schmidt, D. Struve, A. Walter, F. P. Montforts, Helv. Chim. Acta 1998, 81, 1978
    • useful modification of the more convenient unsaturated sulfones in place of nitro olefins was first developed in: b) Y. Abel, E. Haake, G. Haake, W. Schmidt, D. Struve, A. Walter, F. P. Montforts, Helv. Chim. Acta 1998, 81, 1978.
  • 85
    • 0037203153 scopus 로고    scopus 로고
    • Porphyrins 5 belong to the same structural class as tetracyclohexenoporphyrins and other β-octasubstituted porphyrins that all possess enhanced basicity of the inner nitrogens: O. S. Finikova, A. V. Cheprakov, P. J. Carroll, S. Dalosto, S. A. Vinogradov, Inorg. Chem. 2002, 41, 6944-6946.
    • Porphyrins 5 belong to the same structural class as tetracyclohexenoporphyrins and other β-octasubstituted porphyrins that all possess enhanced basicity of the inner nitrogens: O. S. Finikova, A. V. Cheprakov, P. J. Carroll, S. Dalosto, S. A. Vinogradov, Inorg. Chem. 2002, 41, 6944-6946.
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    • 0001688871 scopus 로고    scopus 로고
    • Eds, K. M. Kadish, K. M. Smith, R. Guilard, Academic Press, New York
    • M. O. Senge in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 1999, vol. 2, pp. 239-347.
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    • Senge, M.O.1
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    • 34447543502 scopus 로고    scopus 로고
    • [8c] Ni complex of porphyrin 6a is obtained by aromatization of the respective Ni complex of hexadecahydro TBP in 25-30% yield, and Ni cannot be withdrawn from this complex to afford free base 6a by any means. Alternatively, for the respective Cu complexes aromatization gives 60% yield of Cu-6a, which can be demetallated to give free base 6a in 80% yield, which overall amounts to as low as 48% yield of free base 6a.
    • [8c] Ni complex of porphyrin 6a is obtained by aromatization of the respective Ni complex of hexadecahydro TBP in 25-30% yield, and Ni cannot be withdrawn from this complex to afford free base 6a by any means. Alternatively, for the respective Cu complexes aromatization gives 60% yield of Cu-6a, which can be demetallated to give free base 6a in 80% yield, which overall amounts to as low as 48% yield of free base 6a.
  • 96
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    • [8d] Interestingly, very similar narrow and split Soret bands were recently observed in 5,15-dialkynyl and 5-alkynyl-15-alkenylte- trabenzoporphyrins reported in: H. Yamada, K. Kushibe, T. Okujima, H. Uno, N. Ono, Chem. Commun. 2006, 383-385.
    • [8d] Interestingly, very similar narrow and split Soret bands were recently observed in 5,15-dialkynyl and 5-alkynyl-15-alkenylte- trabenzoporphyrins reported in: H. Yamada, K. Kushibe, T. Okujima, H. Uno, N. Ono, Chem. Commun. 2006, 383-385.
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    • Moreover, there are sparse literature data on electronic absorption spectra of 5,10-disubstituted as well as 5-monosubstituted tetrabenzoporphyrins, which betray that all these systems may also belong to the same structural class:a M. Yasuike, T. Yamaoka, O. Ohno, K. Ichimura, H. Morii, M. Sakuragi, Inorg. Chim. Acta 1991, 185, 39-47;
    • Moreover, there are sparse literature data on electronic absorption spectra of 5,10-disubstituted as well as 5-monosubstituted tetrabenzoporphyrins, which betray that all these systems may also belong to the same structural class:a) M. Yasuike, T. Yamaoka, O. Ohno, K. Ichimura, H. Morii, M. Sakuragi, Inorg. Chim. Acta 1991, 185, 39-47;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.