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Volumn 71, Issue 15, 2006, Pages 5792-5795

A convenient method for the synthesis of 2,5-difunctionalized phospholes bearing ester groups

Author keywords

[No Author keywords available]

Indexed keywords

LIGHT EMISSION; OLEFINS; OPTICAL PROPERTIES; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33746338281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0605748     Document Type: Article
Times cited : (45)

References (66)
  • 4
    • 0003607021 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford
    • (d) Quin, L. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996; Vol. 2.
    • (1996) Comprehensive Heterocyclic Chemistry , vol.2
    • Quin, L.D.1
  • 16
    • 0345463658 scopus 로고
    • Phospholes bearing one carbonyl functional group at the 2- or 5-position have been reported. (a) Mathey, F. Tetrahedron Lett. 1973, 3255.
    • (1973) Tetrahedron Lett. , pp. 3255
    • Mathey, F.1
  • 43
    • 33845278626 scopus 로고
    • For the syntheses of 2,5-disubstituted phospholes via zirconacyclopentadienes (Fagan-Nugent method), see: (a) Pagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2310
    • Pagan, P.J.1    Nugent, W.A.2
  • 53
    • 33746362713 scopus 로고    scopus 로고
    • note
    • In this reaction, the temperature should be kept at -50 °C during the formation of the titanacycle. Below or above this temperature, the yield of 4a decreased significantly.
  • 57
    • 33746338373 scopus 로고    scopus 로고
    • note
    • Compounds 1a-h were prepared from the corresponding terminal-free diynes in one or two steps.
  • 58
    • 33746338056 scopus 로고    scopus 로고
    • note
    • w = 0.1221, R = 0.0503 (I > 2.00σ(I)), GOF = 1.16.
  • 61
    • 33746353807 scopus 로고    scopus 로고
    • note
    • 1H NMR and mass spectrometry.
  • 62
    • 33746323773 scopus 로고    scopus 로고
    • note
    • Fluorescence quantum yields of 4e and 4g relative to quinine sulfate were determined to be 0.074 and 0.088%, respectively.
  • 63
    • 0036060925 scopus 로고    scopus 로고
    • Reáu and co-workers have extensively studied the optical properties of 2,5-diarylphosphole derivatives and disclosed the important role of an intramolecular charge-transfer interaction enforced by the presence of different types of aryl substituents, such as thienyl and pyridyl groups. See: (a) Fave, C.; Hissler, M.; Sénéchal, K.; Ledoux, I.; Zyss, J.; Réau, R. Chem. Commun. 2002, 1674.
    • (2002) Chem. Commun. , pp. 1674
    • Fave, C.1    Hissler, M.2    Sénéchal, K.3    Ledoux, I.4    Zyss, J.5    Réau, R.6
  • 65
    • 33746336788 scopus 로고    scopus 로고
    • note
    • 2 (382, 479); DMF (384, 485).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.