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Volumn 45, Issue 38, 2006, Pages 6294-6296

Tandem ring expansion of alkenyl benzocyclobutenol derivatives into substituted naphthols

Author keywords

Halogenation; Polyaromatic compounds; Reductive coupling; Ring expansion; Strained molecules

Indexed keywords

AROMATIC COMPOUNDS; HALOGENATION; SAMARIUM COMPOUNDS; SUBSTITUTION REACTIONS;

EID: 33749241708     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602428     Document Type: Article
Times cited : (37)

References (34)
  • 7
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    • Angew. Chem. Int. Ed. 2004, 43, 3167-3171;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3167-3171
  • 11
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    • For a related iodonium-mediated ring expansion of alkenyl cyclobutanols, see: a) H. Nemoto, M. Shiraki, K. Fukumoto, J. Org. Chem. 1996, 61, 1347-1353;
    • (1996) J. Org. Chem. , vol.61 , pp. 1347-1353
    • Nemoto, H.1    Shiraki, M.2    Fukumoto, K.3
  • 12
    • 0001347647 scopus 로고
    • related acid-catalyzed ring expansions of alkenyl cyclobutenols and alkenyl benzocyclobutenols were also reported; see: b) G. B. Stone, L. S. Liebeskind, J. Org. Chem. 1990, 55, 4614-4622;
    • (1990) J. Org. Chem. , vol.55 , pp. 4614-4622
    • Stone, G.B.1    Liebeskind, L.S.2
  • 19
    • 33644522056 scopus 로고    scopus 로고
    • related reductive cyclization of bromoalkyl ketones and subsequent ring opening of cycloalkanol derivatives were reported: c) E. Hasegawa, H. Tsuchida, M. Tamura, Chem. Lett. 2005, 1688-1689;
    • (2005) Chem. Lett. , pp. 1688-1689
    • Hasegawa, E.1    Tsuchida, H.2    Tamura, M.3
  • 22
    • 0034729937 scopus 로고    scopus 로고
    • related 5→6 ring enlargement of methanoindane to aryl naphthalene was also reported: f) K. Wakasugi, Y. Nishii, Y. Tanabe, Tetrahedron Lett. 2000, 41, 5937-5942;
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5937-5942
    • Wakasugi, K.1    Nishii, Y.2    Tanabe, Y.3
  • 24
    • 33749258481 scopus 로고    scopus 로고
    • note
    • When the reaction was performed without HMPA, the yield of 4 decreased to 46% and was accompanied by cyclopropanol 3 (16%).
  • 25
    • 33749234693 scopus 로고    scopus 로고
    • note
    • 2O), giving naphthalene 4 in 48% yield.
  • 28
    • 33749247730 scopus 로고    scopus 로고
    • note
    • Previously, we reported the thermolysis of alkenyl benzocyclobutenes that have alkyl groups at the β position of the olefin with Z geometry, whereby mainly a 1,7-hydrogen shift occurred to give the ring-opened 1,3-diene derivatives as the major products; see references [2c] and [2d].
  • 29
    • 33749241252 scopus 로고    scopus 로고
    • note
    • For details, see the Supporting Information.
  • 33
    • 33749241820 scopus 로고    scopus 로고
    • CCDC-611287 (21) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.