메뉴 건너뛰기




Volumn , Issue 7, 2000, Pages 1335-1344

Cycloaddition of acyclic conjugated dienes with a tetrachloro- substituted oxyallyl intermediate generated from pentachloroacetone

Author keywords

Cycloheptenones; Dehydrochlorination; Tropolones; Tropones; 4+3 Cycloaddition

Indexed keywords

ALKADIENE; TROPOLONE DERIVATIVE; TROPONE DERIVATIVE;

EID: 0141576958     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1335::AID-EJOC1335>3.0.CO;2-2     Document Type: Article
Times cited : (16)

References (45)
  • 6
    • 33845470425 scopus 로고
    • An oxyallyl ion pair (3) is expected to be formed from PCA (1) by initial ionization of the enolate anion (2), which is followed by dissociation to the "free" oxyallyl intermediate (6). In TFE, a strong hydrogen bond between the solvent and the negative charge on the oxygen atom would be expected, leading in the extreme case to the 1,1,3,3,-tetrachloro-2-hydroxyallylium chloride ion pair and O-protonated oxyallyl species derived therefrom. Calculations on the unsubstituted oxyallyl prototype have suggested strong diradicaloid character rather than dipolar structures for these intermediates Perchloro substitution should stabilize the oxyallyl intermediate in any case. For ab initio calculations, see: [2a] Y. Osamura, W. T. Borden, K. Morokuma, J. Am. Chem. Soc. 1984, 106, 5112-5115.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5112-5115
    • Osamura, Y.1    Borden, W.T.2    Morokuma, K.3
  • 10
    • 0342357768 scopus 로고
    • B. Föhlisch, E. Gehrlach, G. Henle, U. Boberlin, R. Herter, J. Chem. Res. (S) 1991, 136; J. Chem. Res. (M) 1991, 1462-1492.
    • (1991) J. Chem. Res. (M) , pp. 1462-1492
  • 12
    • 0342792808 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-127329. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax (internat.) +44-1223/ 336-033: E-mail: deposit@ccdc.cam.ac.uk]
    • Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-127329. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax (internat.) +44-1223/ 336-033: E-mail: deposit@ccdc.cam.ac.uk].
  • 13
    • 1542390333 scopus 로고    scopus 로고
    • For recent calculations supporting the stepwise fashion of cycloaddition of the 2-hydroxyallyl cation with 1,3-dienes, see: C. J. Cramer, S. E. Barrows, J. Org. Chem. 1998, 63, 5523-5532.
    • (1998) J. Org. Chem. , vol.63 , pp. 5523-5532
    • Cramer, C.J.1    Barrows, S.E.2
  • 25
    • 4244186266 scopus 로고
    • Patent 893228 (Apr. 4, 1962)
    • Shell Internationale Research Maatschappij, N.V., Brit. Patent 893228 (Apr. 4, 1962); Chem. Abstr. 1962, 57, P9694c.
    • (1962) Chem. Abstr. , vol.57
  • 29
  • 30
    • 0003958840 scopus 로고
    • Non-benzenoid conjugated carbocyclic compounds
    • Elsevier, Amsterdam
    • [19b] For an overview, see: D. Lloyd, Non-benzenoid Conjugated Carbocyclic Compounds (Studies in Organic Chemistry, vol. 16), Elsevier, Amsterdam, 1984, p. 109.
    • (1984) Studies in Organic Chemistry , vol.16 , pp. 109
    • Lloyd, D.1
  • 34
    • 0343227384 scopus 로고    scopus 로고
    • Dissertation, Univ. Stuttgart
    • H. Korfant, Dissertation, Univ. Stuttgart, 1999.
    • (1999)
    • Korfant, H.1
  • 35
    • 0342357764 scopus 로고
    • [3] whereas with 5-methylfuran-2-carbonitrile no cycloadduct at all could be detected (H. Meining, Diplomarbeit, 1991).
    • (1991) Diplomarbeit
    • Meining, H.1
  • 38
    • 4243311895 scopus 로고
    • B. L. Dyatkin, E. P. Mochalina, Izv. Akad. Nauk SSSR, Ser. Khim. 1964, 1225-1229; Bull. Acad. Sci. USSR, Division of Chemical Science (Engl. Transl.) 1964, 1136-1139; Chem. Abstr. 1964, 61, 11881f.
    • (1964) Chem. Abstr. , vol.61


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.