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Volumn 74, Issue 14, 2009, Pages 4927-4933

Oxazolochlorins. 2. Intramolecular Cannizzaro reaction of meso-tetraphenylsecochlorin bisaldehyde

Author keywords

[No Author keywords available]

Indexed keywords

CANNIZZARO REACTION; CHEMICAL EQUATIONS; FREE BASE; H NMR SPECTROSCOPY; OXAZOLE; REACTION CONDITIONS; X RAY DIFFRACTOMETRY;

EID: 67650351983     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9006046     Document Type: Article
Times cited : (46)

References (60)
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  • 2
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    • Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
    • (b) Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 55-124.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 55-124
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  • 3
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    • Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego
    • (c) Lash, T. D. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 125-200.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 125-200
    • Lash, T.D.1
  • 4
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    • For recent leading examples, see: a
    • For recent leading examples, see: (a) Muthiah, C.; Bhaumik, J.; Lindsey, J. S. J. Org. Chem. 2007, 72, 5839-5842.
    • (2007) J. Org. Chem , vol.72 , pp. 5839-5842
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  • 14
    • 0001935323 scopus 로고
    • For reviews covering chlorin syntheses, see: a
    • For reviews covering chlorin syntheses, see: (a) Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126.
    • (1988) Adv. Heterocycl. Chem , vol.43 , pp. 73-126
    • Flitsch, W.1
  • 42
    • 67650422789 scopus 로고    scopus 로고
    • The decomposition is often accompanied by the forming of a green, polar (Rf) 0.10, silica-CH2Cl2, and unstable compound. We tentatively assigned it, based on its morpholinochlorin-like UV-vis spectrum and mass ESI+ HR-MS, 100% MeCN, m/z found 665.2548, corresponding to C44H33N4O3, expected mass 665.2553, as the hydrate structure 2H2·; H2O. Correspondingly, it can be converted by addition of EtOH, under acid catalysis, in high yield to morpholinochlorin 1H2. However, attempts to isolate and fully characterize this compound failed, Chemical Equation Presented
    • 2. However, attempts to isolate and fully characterize this compound failed. (Chemical Equation Presented)
  • 44
    • 67650422791 scopus 로고    scopus 로고
    • Intramolecular Cannizzaro reactions of aromatic vic-bisaldehydes: (b) McDonald, R. S.; Sibley, C. E. Can. J. Chem. 1981, 59, 1061-1067.
    • Intramolecular Cannizzaro reactions of aromatic vic-bisaldehydes: (b) McDonald, R. S.; Sibley, C. E. Can. J. Chem. 1981, 59, 1061-1067.
  • 47
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    • Ph.D. Thesis, University of Connecticut
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    • (2003)
    • McCarthy, J.R.1
  • 50
    • 67650483858 scopus 로고    scopus 로고
    • All the assignments were backed by H,H and H,C-COSY measurements; see the Supporting Information
    • All the assignments were backed by H,H and H,C-COSY measurements; see the Supporting Information.
  • 52
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    • Review article
    • (b) Review article: Fox, S.; Boyle, R. W. Tetrahedron 2006, 62, 10039-10054.
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    • For examples of the 1H NMR shifts expressed by directly β,β′-linked porphyrin dimers, see: (b) Bringmann, G, Götz, D. C. G, Gulder, T. A. M, Gehrke, T. H, Bruhn, T, Kupfer, T, Radacki, K, Braunschweig, H, Heckmann, A, Lambert, C. J. Am. Chem. Soc. 2008, 133, 17812-17825
    • 1H NMR shifts expressed by directly β,β′-linked porphyrin dimers, see: (b) Bringmann, G.; Götz, D. C. G.; Gulder, T. A. M.; Gehrke, T. H.; Bruhn, T.; Kupfer, T.; Radacki, K.; Braunschweig, H.; Heckmann, A.; Lambert, C. J. Am. Chem. Soc. 2008, 133, 17812-17825.
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    • (a) Shelnutt, J. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 7, pp 167-224.
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    • Shelnutt, J.A.1
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.