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Volumn 105, Issue 11, 1983, Pages 3720-3722

Vinyl Radical Cyclization. 2. Dicyclization via Selective Formation of Unsaturated Vinyl Radicals by Intramolecular Addition to Triple Bonds. Applications to the Synthesis of Butenolides and Furans

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EID: 0000516559     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00349a067     Document Type: Letter
Times cited : (200)

References (9)
  • 2
    • 0009106181 scopus 로고
    • Gazith, M.; Szwarc, M. J. Am. Chem. Soc. 1957, 79, 3339. Abel, P. I. In “Comprehensive Chemical Kinetics” Bamford, C. H., Tripper, C. F. H., Eds.; Elsevier: Amsterdam, 1976; Vol. 18. Giese, B.; Lachhein, S. Angew. Chem. 1982, 94, 780.
    • Kharasch, M. S.; Jerome, J. J.; Urry, W. H. J. Org. Chem. 1950, 15, 966. Gazith, M.; Szwarc, M. J. Am. Chem. Soc. 1957, 79, 3339. Abel, P. I. In “Comprehensive Chemical Kinetics” Bamford, C. H., Tripper, C. F. H., Eds.; Elsevier: Amsterdam, 1976; Vol. 18. Giese, B.; Lachhein, S. Angew. Chem. 1982, 94, 780.
    • (1950) J. Org. Chem. , vol.15 , pp. 966
    • Kharasch, M.S.1    Jerome, J.J.2    Urry, W.H.3
  • 3
    • 0000432088 scopus 로고
    • For a recent example of an intramolecular addition of a carbon-centered radical to a triple bond, see:
    • For a recent example of an intramolecular addition of a carbon-centered radical to a triple bond, see: Hart, D. J.; Choi, J.-K.; Tsai, Y.-M. Tetrahedron Lett. 1982, 23, 4765.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4765
    • Hart, D.J.1    Choi, J.-K.2    Tsai, Y.-M.3
  • 4
    • 0002714675 scopus 로고
    • Reaction products were examined by capillary GLC, NMR, and IR spectroscopy and, in the case of 12, by mass spectrometry (M+ 284.286). Cyclizations were run under an argon atmosphere. Purification was by flash chromatography).
    • Reaction products were examined by capillary GLC, NMR, and IR spectroscopy and, in the case of 12, by mass spectrometry (M+ 284.286). Cyclizations were run under an argon atmosphere. Purification was by flash chromatography (Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923).
    • (1978) J. Org. Chem. , vol.43 , pp. 2923
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 6
    • 0000016262 scopus 로고
    • The beneficial effect of β-alkoxy groups in radical cyclization reactions into a double bond has been noted:
    • The beneficial effect of β-alkoxy groups in radical cyclization reactions into a double bond has been noted: Beckwith, A. L. J.; Blair, I.; Phil-lipou, G. J. Am. Chem. Soc. 1974, 96, 1613.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 1613
    • Beckwith, A.L.J.1    Blair, I.2    Phil-lipou, G.3
  • 8
    • 0000539789 scopus 로고
    • For other recent routes to β-substituted furans, see (a), (b) McMurry, J. E.; Donovan, S. F. Tetrahedron Lett. 1977, 2869.
    • For other recent routes to β-substituted furans, see (a) Tanis, S. P. Tetrahedron Lett. 1982, 23, 3115. (b) McMurry, J. E.; Donovan, S. F. Tetrahedron Lett. 1977, 2869.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3115
    • Tanis, S.P.1
  • 9
    • 0037540307 scopus 로고
    • These monocyclizations were also conveniently performed by using a polystyrene-supported tributyltin hydride first prepared in this laboratory by Gary Tennyson, following essentially the route described for the related dihydride).
    • These monocyclizations were also conveniently performed by using a polystyrene-supported tributyltin hydride first prepared in this laboratory by Gary Tennyson, following essentially the route described for the related dihydride (Weinshenker, N. M.; Crosby, G. A.; Wong, J.Y. J. Org. Chem. 1975, 40, 1966).
    • (1975) J. Org. Chem. , vol.40 , pp. 1966
    • Weinshenker, N.M.1    Crosby, G.A.2    Wong, J.Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.