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Volumn 69, Issue 19, 2004, Pages 6404-6412

Meso-substituted [34]octaphyrin(1.1.1.0.1.1.1.0) and corrole formation in reactions of a dipyrromethanedicarbinol with 2,2′-bipyrrole

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AROMATIC HYDROCARBONS; CATALYSTS; METHANE; REACTION KINETICS; SOLVENTS; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

EID: 4644302429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049131z     Document Type: Article
Times cited : (42)

References (46)
  • 2
    • 0000605623 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (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
  • 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
  • 23
    • 0012638773 scopus 로고    scopus 로고
    • After a report of our preliminary results,9a Decreay and Collman published the observation of corrole formation in modest yield from a dipyrromethanedicarbinol + 2,2′-bipyrrole route.9b In a recent review article on corrole synthesis,9c Gryko reported that his group has also attempted to prepare meso-substituted corrole via 2,2′-bipyrrole but without success. To the best of our knowledge, the details of their work have not been published. (a) Geier, G. R., III; Grindrod, S. C.; Callinan, J. B.; Reid, C. G. Abstr. Papers Am. Chem. Soc. 2002, 224, 750.
    • (2002) Abstr. Papers Am. Chem. Soc. , vol.224 , pp. 750
    • Geier III, G.R.1    Grindrod, S.C.2    Callinan, J.B.3    Reid, C.G.4
  • 32
    • 4644259359 scopus 로고    scopus 로고
    • note
    • Although 2,2′-bipyrrole is now commercially available (Alfa Aesar), its relatively high price (1 g, $224) provided the impetus to further improve its synthesis.
  • 34
    • 4644281598 scopus 로고    scopus 로고
    • note
    • We considered the possibility that DDQ might interfere with the detection of HPO as we had observed to be the case in our previous studies involving the synthesis of TPC.11 Thus, samples were washed with an aqueous basic dithionite solution prior to analysis by TLC and UV-vis.
  • 35
    • 4644317192 scopus 로고    scopus 로고
    • note
    • As it turned out, TPC was rarely produced in reactions of 1a-OH with 3 according to TLC analysis; thus, it was not typically necessary to determine the yield of TPC in the presence of HPO.
  • 37
    • 4644229810 scopus 로고    scopus 로고
    • note
    • 2 required brief sonication in order to produce a solution of bipyrrole that was not visibly light scattering.
  • 38
    • 4644273837 scopus 로고    scopus 로고
    • note
    • The quantity of acid is reported in concentration units of molarity for convenience of comparison of reaction conditions; however, these four acids are poorly soluble and the reaction mixtures were generally heterogeneous as reported previously.12
  • 42
    • 4644336708 scopus 로고    scopus 로고
    • note
    • 2 was used to elute HpFPO from the silica pad.
  • 43
    • 4644294040 scopus 로고    scopus 로고
    • note
    • We did not attempt to use p-chloranil because DDQ did not appear to interfere with the isolation of HpFPO, and we had previously encountered difficulties when attempting to use p-chloranil in the synthesis of TpFPC.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.