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Volumn 62, Issue 26, 1997, Pages 9251-9260

Synthesis and characterization of all-alkyl-substituted mono-, di-, and trioxosapphyrins

Author keywords

[No Author keywords available]

Indexed keywords

3,7,18,22 TETRAETHYL 2,8,12,13,17,23 HEXAMETHYL 15,27,29 TRIOXASAPPHYRIN; 3,7,18,22 TETRAETHYL 2,8,12,13,17,23 HEXAMETHYL 27 OXASAPPHYRIN; 3,8,12,13,17,22 HEXAETHYL 2,7,18,23 TETRAMETHYL 15,29 DIOXASAPPHYRIN; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; HYDROCHLORIC ACID; MACROCYCLIC COMPOUND; PORPHYRIN DERIVATIVE; SAPPHYRIN; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

EID: 0031450710     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715736     Document Type: Article
Times cited : (45)

References (34)
  • 10
    • 33751156933 scopus 로고
    • Other syntheses of sapphyrin that are not predicated on the use of tripyrranes have been reported recently: (a) Sessler, J. L.; Lisowski, J.; Boudreaux, K. A.; Lynch, V.; Barry, J.; Kodadek, T. J. J. Org. Chem. 1995, 60, 5975. (b) Latos-Grazynski, L.; Rachlewics, K. Chem. Eur. J. 1995, 1, 68. (c) Paolesse, R.; Licoccia, S.; Spagnoli, M.; Boschi, T.; Khoury, R. G.; Smith, K. J. Org. Chem. 1997, 62, 5133.
    • (1995) J. Org. Chem. , vol.60 , pp. 5975
    • Sessler, J.L.1    Lisowski, J.2    Boudreaux, K.A.3    Lynch, V.4    Barry, J.5    Kodadek, T.J.6
  • 11
    • 0003982087 scopus 로고
    • Other syntheses of sapphyrin that are not predicated on the use of tripyrranes have been reported recently: (a) Sessler, J. L.; Lisowski, J.; Boudreaux, K. A.; Lynch, V.; Barry, J.; Kodadek, T. J. J. Org. Chem. 1995, 60, 5975. (b) Latos-Grazynski, L.; Rachlewics, K. Chem. Eur. J. 1995, 1, 68. (c) Paolesse, R.; Licoccia, S.; Spagnoli, M.; Boschi, T.; Khoury, R. G.; Smith, K. J. Org. Chem. 1997, 62, 5133.
    • (1995) Chem. Eur. J. , vol.1 , pp. 68
    • Latos-Grazynski, L.1    Rachlewics, K.2
  • 12
    • 0030842359 scopus 로고    scopus 로고
    • Other syntheses of sapphyrin that are not predicated on the use of tripyrranes have been reported recently: (a) Sessler, J. L.; Lisowski, J.; Boudreaux, K. A.; Lynch, V.; Barry, J.; Kodadek, T. J. J. Org. Chem. 1995, 60, 5975. (b) Latos-Grazynski, L.; Rachlewics, K. Chem. Eur. J. 1995, 1, 68. (c) Paolesse, R.; Licoccia, S.; Spagnoli, M.; Boschi, T.; Khoury, R. G.; Smith, K. J. Org. Chem. 1997, 62, 5133.
    • (1997) J. Org. Chem. , vol.62 , pp. 5133
    • Paolesse, R.1    Licoccia, S.2    Spagnoli, M.3    Boschi, T.4    Khoury, R.G.5    Smith, K.6
  • 21
    • 0000264981 scopus 로고
    • Wiley: New York, Collect
    • (a) Burness, D. M. Organic Synthesis; Wiley: New York, 1963; Collect. Vol. IV, p 649.
    • (1963) Organic Synthesis , vol.4 , pp. 649
    • Burness, D.M.1
  • 25
    • 15444340354 scopus 로고    scopus 로고
    • U.S. Patent 2,760,986, 1956
    • (c) Fletcher, G. L.; Hull, J. S. U.S. Patent 2,760,986, 1956.
    • Fletcher, G.L.1    Hull, J.S.2
  • 31
    • 15444360801 scopus 로고    scopus 로고
    • note
    • The use of a solvent system different from that employed in the case of the all-aza sapphyrin 4 resulted from an inability to effect oxidation of the furan containing dihydrosapphyrins in ethanol. Various oxidants, air, DDQ, and chloranil were tried, but in no case did oxidation to the fully conjugated oxosapphyrin occur. Use of a halogenated solvent system on the other hand, allowed these critical oxidations to be effected readily in what is literally a one-pot procedure.
  • 32
    • 15444347856 scopus 로고    scopus 로고
    • note
    • Although the dihydrosapphyrin intermediates will oxidize if left in solution exposed to air (roughly 10, 24, and 48 h in the case of the mono-, di-, and trioxasapphyrins, respectively), extensive decomposition is detected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.