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Volumn 73, Issue 21, 2008, Pages 8189-8197

The curtius rearrangement of cyclopropyl and cyclopropenoyl azides. a combined theoretical and experimental mechanistic study

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CHEMICAL BONDS; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; EXPERIMENTS; GAS DYNAMICS; GASES; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROPANE; PROPYLENE;

EID: 55249126161     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801104t     Document Type: Article
Times cited : (27)

References (56)
  • 5
    • 0003917975 scopus 로고
    • Scriven, E. F. V, Ed, Academic Press: New York
    • (e) Lwowski, W. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984; p 205.
    • (1984) Azides and Nitrenes , pp. 205
    • Lwowski, W.1
  • 6
    • 55249108800 scopus 로고    scopus 로고
    • 2 by the Curtius reaction with 99.3% retention of configuration. The correspondingly related Schmidt, Hofmann, Lossen, and Beckman reactions also all proceed with essentially complete retention of configuration. See: Campell, A.; Kenyon, J. J. Chem. Soc. 1946, 25.
    • 2 by the Curtius reaction with 99.3% retention of configuration. The correspondingly related Schmidt, Hofmann, Lossen, and Beckman reactions also all proceed with essentially complete retention of configuration. See: Campell, A.; Kenyon, J. J. Chem. Soc. 1946, 25.
  • 9
    • 0040981211 scopus 로고
    • For a thorough discussion of early mechanistic proposals on the Curtius rearrangement, see: c, de Mayo, P, Ed, Interscience Publishers: New York
    • For a thorough discussion of early mechanistic proposals on the Curtius rearrangement, see: (c) Smith, P. A. In Molecular Rearrangements; de Mayo, P., Ed.; Interscience Publishers: New York, 1963; pp 457-591.
    • (1963) Molecular Rearrangements , pp. 457-591
    • Smith, P.A.1
  • 19
    • 55249125308 scopus 로고    scopus 로고
    • The photochemical Curtius rearrangement may take place via concerted rearrangement of the acyl azide or via a stepwise mechanism that involves an acylnitrene. For experimental work on the photo-Curtius rearrangement, see refs 1e, 4e, and 4a and references therein
    • (a) The photochemical Curtius rearrangement may take place via concerted rearrangement of the acyl azide or via a stepwise mechanism that involves an acylnitrene. For experimental work on the photo-Curtius rearrangement, see refs 1e, 4e, and 4a and references therein.
  • 21
    • 0001167403 scopus 로고    scopus 로고
    • For computations on the Curtius rearrangements of acylnitrenes, see refs 4a, 6, and (a) Sigman, M. E.; Autrey, T.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 4297.
    • For computations on the Curtius rearrangements of acylnitrenes, see refs 4a, 6, and (a) Sigman, M. E.; Autrey, T.; Schuster, G. B. J. Am. Chem. Soc. 1988, 110, 4297.
  • 36
    • 0037134198 scopus 로고    scopus 로고
    • and references therein
    • (b) Bach, R. D.; Dmitrenko, O. J. Org. Chem. 2002, 67, 2588, and references therein.
    • (2002) J. Org. Chem , vol.67 , pp. 2588
    • Bach, R.D.1    Dmitrenko, O.2
  • 39
    • 55249123924 scopus 로고    scopus 로고
    • Frisch, M. J. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
    • (a) Frisch, M. J. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
  • 40
    • 55249124637 scopus 로고    scopus 로고
    • Gaussian 03, revision B.05 (SGI64-G03RevB.05); Gaussian, Inc.: Pittsburgh, PA, 2003. See the Supporting Information for the full list of authors.
    • (b) Gaussian 03, revision B.05 (SGI64-G03RevB.05); Gaussian, Inc.: Pittsburgh, PA, 2003. See the Supporting Information for the full list of authors.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.