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Volumn 45, Issue 24, 2004, Pages 4711-4714

Intramolecular formal [4+2] cycloaddition reactions of secondary and tertiary aryldiacetylene alcohols

Author keywords

Biradicals; Cycloaromatization; Intramolecular 4+2 cycloadditions; Methylene quinone; Propargyl alcohols

Indexed keywords

ACETYLENE DERIVATIVE; ALCOHOL DERIVATIVE; CHLORIDE; DIKETONE; QUINONE DERIVATIVE; XANTHENE;

EID: 2442646215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.096     Document Type: Article
Times cited : (16)

References (26)
  • 16
    • 2442673274 scopus 로고    scopus 로고
    • note
    • The evidence in favour of the transposed propargyl chloride 7a, as against the isomeric structure resulting from direct substitution of the hydroxyl group of 6a, was obtained from NOE experiments: irradiation of the propargyl hydrogen at 6.51 ppm enhanced a complex aromatic signal attributed to the two ortho protons of the propargyl phenyl ring
  • 17
    • 0000711103 scopus 로고
    • The presence of acids favours both yield and kinetics in thermal cycloaromatization reactions:
    • The presence of acids favours both yield and kinetics in thermal cycloaromatization reactions: Danheiser R.L., Gould A.E., Fernández de la Pradilla F., Helgason A.L. J. Org. Chem. 59:1994;5514-5515
    • (1994) J. Org. Chem. , vol.59 , pp. 5514-5515
    • Danheiser, R.L.1    Gould, A.E.2    Fernández De La Pradilla, F.3    Helgason, A.L.4
  • 18
    • 2442651974 scopus 로고    scopus 로고
    • note
    • 2 and final reaction with lithium phenylacetylide
  • 21
    • 2442684646 scopus 로고    scopus 로고
    • note
    • All new compounds were fully characterized spectroscopically and had satisfactory elemental analyses or HRMS data
  • 22
    • 0035974390 scopus 로고    scopus 로고
    • in 63% overall yield by Stille coupling with tributyl(phenylpropynyl)tin followed by reaction with lithium phenylacetylide
    • Compound 6c was synthesized from 1-bromo-4-methoxyxanthone ( García A., Domínguez D. Tetrahedron Lett. 42:2001;5219-5221. ) in 63% overall yield by Stille coupling with tributyl(phenylpropynyl)tin followed by reaction with lithium phenylacetylide
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5219-5221
    • García, A.1    Domínguez, D.2
  • 23
    • 2442638158 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure 14 in this paper, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-211466. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk)
  • 24
    • 0013189851 scopus 로고
    • Formation of allenyl acetates and benzoates by thermal or metal-catalyzed rearrangement of the corresponding isomeric propargyl derivatives is well documented:
    • Formation of allenyl acetates and benzoates by thermal or metal-catalyzed rearrangement of the corresponding isomeric propargyl derivatives is well documented: Oelberg D.G., Schiavelli M.D. J. Org. Chem. 42:1977;1804-1806
    • (1977) J. Org. Chem. , vol.42 , pp. 1804-1806
    • Oelberg, D.G.1    Schiavelli, M.D.2
  • 25
    • 0042747502 scopus 로고
    • Examples of trapping of the initially formed biradical in acyclic enyne-allenes by a carbon-carbon double bond in a 5-exo mode:
    • Examples of trapping of the initially formed biradical in acyclic enyne-allenes by a carbon-carbon double bond in a 5-exo mode: Andemichael Y.W., Gu Y.G., Wang K.K. J. Org. Chem. 57:1992;794-796
    • (1992) J. Org. Chem. , vol.57 , pp. 794-796
    • Andemichael, Y.W.1    Gu, Y.G.2    Wang, K.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.