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Volumn 69, Issue 12, 2004, Pages 4159-4169

A survey of acid catalysis and oxidation conditions in the two-step, one-flask synthesis of meso-substituted corroles via dipyrromethanedicarbinols and pyrrole

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; OXIDATION; PORPHYRINS; THERMAL EFFECTS;

EID: 2942536218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0496493     Document Type: Article
Times cited : (94)

References (51)
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    • (b) Sessler, J. L.; Gebauer, A.; Vogel, E. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 2000; Vol. 2, pp 1-54.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 1-54
    • Sessler, J.L.1    Gebauer, A.2    Vogel, E.3
  • 3
    • 0002484311 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (c) Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 2000; Vol. 2, pp 55-124.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 55-124
    • Sessler, J.L.1    Gebauer, A.2    Weghorn, S.J.3
  • 4
    • 0003314365 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (d) Latos-Grazynski, L. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 2000; Vol. 2, pp 361-416.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 361-416
    • Latos-Grazynski, L.1
  • 9
    • 0001674837 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (b) Paolesse, R. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 2000; Vol. 2, pp 201-232.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 201-232
    • Paolesse, R.1
  • 12
    • 0000694165 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (c) Erben, C.; Will, S.; Kadish, K. M. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 2000; Vol. 2, pp 233-300.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 233-300
    • Erben, C.1    Will, S.2    Kadish, K.M.3
  • 40
    • 0035528864 scopus 로고    scopus 로고
    • TPP is expected to only arise from reaction of a dipyrromethanedicarbinol with pyrrole under reversible conditions (by analogy to reactions of 5-phenyldipyrromethane). Geier, G. R., III; Littler, B. J.; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 701-711.
    • (2001) J. Chem. Soc., Perkin Trans. 2 , pp. 701-711
    • Geier III, G.R.1    Littler, B.J.2    Lindsey, J.S.3
  • 41
    • 2942523925 scopus 로고    scopus 로고
    • note
    • max of the Soret bands of porphyrin and corrole and the greater molar extinction coefficient of the porphyrin. In our reaction route, porphyrin can only arise as the result of undesired reversibility. Thus, spectral monitoring of corrole generated from reactions devoid of scrambling will not suffer from interference due to porphyrin.
  • 47
    • 2942617329 scopus 로고    scopus 로고
    • note
    • 2 and the reaction mixtures were heterogeneous as reported previously.
  • 48
    • 2942553738 scopus 로고    scopus 로고
    • note
    • p-Chloranil lacks the cyano groups that are reportedly important in the interaction between DDQ and porphyrin, 27 and are potentially important in the corresponding interaction of DDQ with corrole.
  • 49
    • 2942523926 scopus 로고    scopus 로고
    • note
    • The aq dithionite wash of crude reaction mixtures on a semipreparative scale is irksome as the mixtures are prone to formation of an emulsion and the organic/aqueous interface is challenging to locate.
  • 51
    • 2942557424 scopus 로고    scopus 로고
    • note
    • The 1H NMR spectral results that we obtained differ slightly from those previously reported for 2b. 14 This likely stems from differences in resolution between the spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.