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Volumn , Issue 22, 2001, Pages 4357-4365

Base-induced solvolyses of [3.2.1]bicyclic α,α′-dichloro ketones - 1,3-transposition and ring-contraction

Author keywords

Carbocycles; Ketones; Rearrangements; Ring contractions; Solvolysis

Indexed keywords

2,4 DICHLOROBICYCLO[3.2.1]OCT 6 EN 3 ONE; ACETAL DERIVATIVE; BASE; KETONE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG; [3.2.1]BICYCLIC ALPHA,ALPHA' DICHLOROKETONE DERIVATIVE;

EID: 0035186505     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200111)2001:22<4357::AID-EJOC4357>3.0.CO;2-O     Document Type: Article
Times cited : (11)

References (35)
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    • N. De Kimpe, R. Verhé, The Chemistry of α-Haloketones, α-Haloaldchydes and α-Haloimines, in Updates from the Chemistry of Functional Groups (Eds.: S. Patai, Z. Rapoport), Wiley, Chichester, 1988.
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  • 12
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    • note
    • MO calculations on the ions 9 and 13, and also its O-protonated equivalents, would be desirable to give further insights into the competing reaction channels affording 10, 11, and 14. To simplify matters in Scheme 1, intermediates are formulated as species with negatively charged oxygen atoms.
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    • (1992)
    • Radl, A.1
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    • note
    • 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-157688. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax int. code + 44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
  • 24
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    • In the latter case the negative charge of the oxyanion intermediate must be put on the "left" oxygen atom of the intermediate. However that would be an irrelevant formalism since rapid prototropy would be established in water. - A SET mechanism might also be considered; for MO calculations see: I. Rajyaguru, H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2 1987, 1819-1827.
    • (1987) J. Chem. Soc., Perkin Trans. 2 , pp. 1819-1827
    • Rajyaguru, I.1    Rzepa, H.S.2
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    • note
    • However, under forced conditions, cyclohexane-1,2-dione also undergoes rearrangement to 1-hydroxycyclopentanecarboxylic acid [ref. 10].
  • 26
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    • A Surrey of Favorskii Rearrangement Mechanisms
    • (Ed.: R. A. Abramovitch), Plenum Press, New York - London
    • [20c] A. Baretta, B. Waegell, A Surrey of Favorskii Rearrangement Mechanisms, in: Reactive Intermediates (Ed.: R. A. Abramovitch), vol. 2, p. 527-585, Plenum Press, New York - London, 1982.
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    • Baretta, A.1    Waegell, B.2
  • 33
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    • note
    • The careful reader will note that the products formed from meso dichlorides are chiral molecules; might the reactions be executed with enantioselective control?
  • 34
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    • note
    • [23) The authors will not continue these investigations and therefore would welcome further research.
  • 35
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    • Prepared with o-phenylenediamine in analogy to the derivative of bornane-2,3-dione (3-oxocamphor): A. Heckendorn, Helv. Chim. Acta 1929, 12, 50-60.
    • (1929) Helv. Chim. Acta , vol.12 , pp. 50-60
    • Heckendorn, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.