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Volumn 69, Issue 11, 2004, Pages 3842-3848

Intramolecular dehydro Diels-Alder reactions of diarylacetylenes: Switching between benzo[b]- and benzo[c]fluorenones as products by controlling the rearrangement of cyclic allene intermediates

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; ISOMERS; MIXTURES; MOLECULAR DYNAMICS; SUBSTITUTION REACTIONS; SWITCHING;

EID: 2442701581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498213     Document Type: Article
Times cited : (65)

References (33)
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  • 11
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    • Benzo[c]fluorene derivatives have been postulated as carcinogenic metabolites: Wang, J.-Q.; Weyand, E. H.; Harvey, R. G. J. Org. Chem. 2002, 67, 6216-6219.
    • (2002) J. Org. Chem. , vol.67 , pp. 6216-6219
    • Wang, J.-Q.1    Weyand, E.H.2    Harvey, R.G.3
  • 12
    • 2442640943 scopus 로고    scopus 로고
    • note
    • Tertiary alcohols gave only 3, and tert-butyl gave 3 and 7 in a 16:1 ratio.
  • 13
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    • On electronic control in the Schmittel and Bergman cyclizations, see: (a) Schmittel, M.; Maywald, M. Chem. Commun. 2001, 155-156.
    • (2001) Chem. Commun. , pp. 155-156
    • Schmittel, M.1    Maywald, M.2
  • 16
    • 0034596432 scopus 로고    scopus 로고
    • (c) Choy, N.; Kim, C.-S.; Ballestero, C.; Artigas, L.; Diez, C.; Lichtenberger, F.; Shapiro, J.; Russell, K. C. Tetrahedron Lett. 2000, 41, 6955-6958. Schmittel, M.; Kiau, S. Chem. Lett. 1995, 953-954.
    • (1995) Chem. Lett. , pp. 953-954
    • Schmittel, M.1    Kiau, S.2
  • 17
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    • Brückner, R. Synlett 1994, 51-53; Liebigs Ann. 1996, C41, 447-456 and 457-471.
    • (1994) Synlett , pp. 51-53
    • Brückner, R.1
  • 18
    • 0001172329 scopus 로고    scopus 로고
    • Brückner, R. Synlett 1994, 51-53; Liebigs Ann. 1996, C41, 447-456 and 457-471.
    • (1996) Liebigs Ann. , vol.C41 , pp. 447-456
  • 21
    • 85085784919 scopus 로고    scopus 로고
    • note
    • 2), silylated benzofluorenones 3′d (30%) and 3′e (80%) were the only products obtained. Attempts to desilylate these compounds led to decomposition.
  • 22
    • 2442679710 scopus 로고    scopus 로고
    • note
    • Relatively low yield obtained (30%) might be due to the moderate thermal instability of 1d.
  • 23
    • 85085784569 scopus 로고    scopus 로고
    • note
    • 3, and NaH, respectively, but attempts at their cyclization all failed because they were thermally unstable and decomposed.
  • 24
    • 2442674705 scopus 로고    scopus 로고
    • note
    • Thermolysis of 1a in the presence of triethylamine gives 3a quantitatively; see ref 5b.
  • 25
    • 2442675957 scopus 로고    scopus 로고
    • note
    • Compounds 1f-o were all prepared in good yields by procedures similar to the one depicted in Scheme 2. See Supporting Information for details.
  • 26
    • 2442665962 scopus 로고    scopus 로고
    • note
    • No desilylation step was necessary in this case.
  • 28
  • 29
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    • 2 symmetry in asymmetric synthesis, see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
    • (1989) Chem. Rev. , vol.89 , pp. 1581
    • Whitesell, J.K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.