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Volumn 68, Issue 8, 2003, Pages 3330-3332

Facile intramolecular cyclization in oxidative coupling of acetylenes linked to 1,3-positions of benzene: Strained [12]metacyclophanedienetetrayne system

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION;

EID: 0037453630     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0268299     Document Type: Article
Times cited : (17)

References (34)
  • 1
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    • The Royal Society of Chemistry: Cambridge
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    • (1991) Cyclophanes
    • Diederich, F.1
  • 9
    • 85047676352 scopus 로고    scopus 로고
    • A similar mechanism was proposed: Fallis, A. G. Can. J. Chem. 1999, 77, 159.
    • (1999) Can. J. Chem. , vol.77 , pp. 159
    • Fallis, A.G.1
  • 13
    • 0037112596 scopus 로고    scopus 로고
    • For representative examples for the formation of small carbon clusters from organic precursors: (a) Prinzbach, H.; Weiler, A.; Landenberger, P.; Wahl, F.; Worth, J.; Scott, L. T.; Gelmont, M.; Olevano, D.; Issendorff, B. v. Nature 2000, 407, 60. (b) Manini, P.; Amrein, W.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. 2002, 41, 4339.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4339
    • Manini, P.1    Amrein, W.2    Gramlich, V.3    Diederich, F.4
  • 14
    • 0344341202 scopus 로고    scopus 로고
    • note
    • Compounds 3a, 3b, and 4 were unseparable mixtures of diastereomers, of which one isomer is drawn for clarity.
  • 15
    • 0029769640 scopus 로고    scopus 로고
    • 2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1556
    • Kawase, T.1    Ueda, N.2    Darabi, H.R.3    Oda, M.4
  • 16
    • 0030767549 scopus 로고    scopus 로고
    • 2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6681
    • Kawase, T.1    Ueda, N.2    Oda, M.3
  • 17
    • 0033245546 scopus 로고    scopus 로고
    • 2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
    • (1999) Chem. Lett. , pp. 745
    • Kawase, T.1    Hosokawa, Y.2    Kurata, H.3    Oda, M.4
  • 18
    • 0035823729 scopus 로고    scopus 로고
    • 2 carbon signals of highly strained, acetylene-bridged metacyclophanes exhibit downfield shifts: (a) Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. (b) Kawase, T.; Ueda, N.; Oda, M. Tetrahedron Lett. 1997, 38, 6681. (c) Kawase, T.; Hosokawa, Y.; Kurata, H.; Oda, M. Chem. Lett. 1999, 745. (d) Hosokawa, Y.; Kawase, T.; Oda, M. Chem. Commun. 2001, 1948.
    • (2001) Chem. Commun. , pp. 1948
    • Hosokawa, Y.1    Kawase, T.2    Oda, M.3
  • 22
    • 0345635614 scopus 로고    scopus 로고
    • note
    • The lowest-field signal of 6 which appeared at 152 ppm was due to the aromatic carbon attached to the tert-butyl group.
  • 23
    • 0002577139 scopus 로고    scopus 로고
    • (a) Similar deshielding effect was observed in a [8]metacyclophanedienediyne system: Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2002, 4, 11.
    • (2002) Org. Lett. , vol.4 , pp. 11
    • Collins, S.K.1    Yap, G.P.A.2    Fallis, A.G.3
  • 24
    • 0344773069 scopus 로고    scopus 로고
    • note
    • w = 0.188.
  • 25
    • 0000831766 scopus 로고
    • Halton, B., Ed.; JAI Press: Greenwich
    • For the definition of the deformations angles of strained cyclophanes, see: Bickelhaupt, F.; de Wolf, W. H. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: Greenwich, 1993; Vol. 3, p 185.
    • (1993) Advances in Strain in Organic Chemistry , vol.3 , pp. 185
    • Bickelhaupt, F.1    De Wolf, W.H.2
  • 28
    • 0345203631 scopus 로고    scopus 로고
    • note
    • For the corresponding cyclobutenyl case, see refs 3 and 4.
  • 31
    • 0344773072 scopus 로고    scopus 로고
    • note
    • For the corresponding cyclobutenyl case, see ref 7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.