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Volumn 71, Issue 22, 2006, Pages 8493-8499

Syntheses of aporphine and homoaporphine alkaloids by intramolecular ortho-arylation of phenols with aryl halides via SRN1 reactions in liquid ammonia

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; DERIVATIVES; MOLECULAR DYNAMICS; PHENOLS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33750477011     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061478+     Document Type: Article
Times cited : (59)

References (48)
  • 1
    • 2642522343 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • Ríos, J. L.; Máñez, S.; Giner, R. M.; Recio, M. C. In The Alkaloids: Cordell, G. A., Ed.; Academic Press: New York, 2000; Vol. 53; pp 57-117.
    • (2000) The Alkaloids , vol.53 , pp. 57-117
    • Ríos, J.L.1    Máñez, S.2    Giner, R.M.3    Recio, M.C.4
  • 19
    • 0001887447 scopus 로고    scopus 로고
    • Paquette, L. A., Bittman, R., Eds.; Wiley & Sons: New York
    • (b) Rossi, R. A.; Pierini, A. B.; Santiago, A. N. In Organic Reactions; Paquette, L. A., Bittman, R., Eds.; Wiley & Sons: New York, 1999; pp 1-271.
    • (1999) Organic Reactions , pp. 1-271
    • Rossi, R.A.1    Pierini, A.B.2    Santiago, A.N.3
  • 20
    • 27444432809 scopus 로고    scopus 로고
    • Griesberck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, Chapter 15
    • (c) Rossi, R. A. In Synthetic Organic Photochemistry; Griesberck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005: Vol. 12, Chapter 15, pp 495-527.
    • (2005) Synthetic Organic Photochemistry , vol.12 , pp. 495-527
    • Rossi, R.A.1
  • 34
    • 0344887064 scopus 로고
    • and references therein
    • a of PhOH is 18.0 in DMSO). See: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463 and references therein.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1
  • 35
    • 33750445798 scopus 로고    scopus 로고
    • note
    • -. (AM1/UHF method).
  • 36
    • 2142819985 scopus 로고    scopus 로고
    • The driving force of the 1,5-hydrogen shift is that secondary aminyl radicals are ca. 15-20 kcal/mol more stable than phenyl radicals (AM1/UHF method). For the bond dissociation energy (BDE) of dimethylamine, see: (a) Feng, Y.; Liu, L.; Wang, J. T.; Zhao, S. W.; Guo, Q. X. J. Org. Chem. 2004, 69, 3129-3138.
    • (2004) J. Org. Chem. , vol.69 , pp. 3129-3138
    • Feng, Y.1    Liu, L.2    Wang, J.T.3    Zhao, S.W.4    Guo, Q.X.5
  • 38
    • 0037393779 scopus 로고    scopus 로고
    • and references therein
    • 3 is 110.4 kcal/mol, whereas for benzene, it is 112.9 kcal/mol. For a review of BDE for organic molecules, see: Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263 and references therein.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 255-263
    • Blanksby, S.J.1    Ellison, G.B.2
  • 45
    • 33750487334 scopus 로고    scopus 로고
    • note
    • The fact that this is the only example of ring closure at the paraposition of the phenoxy group may be due to the more electrophilic character of the 3-fluoro-substituted phenyl radical compared to that of the phenyl radical.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.