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Volumn 37, Issue 13-14, 1998, Pages 1850-1853

A spontaneous fragmentation: From the Criegee zwitterion to coarctate Mobius aromaticity

Author keywords

Aromaticity; Fragmentations; Ozonolysis; Spiro compounds; Transition states

Indexed keywords


EID: 0032479723     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14<1850::AID-ANIE1850>3.0.CO;2-B     Document Type: Article
Times cited : (21)

References (27)
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    • (1994) Angew. Chem. , vol.106 , pp. 261-283
    • Herges, R.1
  • 2
    • 33748716611 scopus 로고
    • R. Herges, Angew. Chem. 1994, 106, 261-283; Angew. Chem. Int. Ed. Engl. 1994, 33, 255-276.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 255-276
  • 4
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    • Butterworths, London
    • T. L. Cottrell, The Strengths of Chemical Bonds, 2nd ed., Butterworths, London, 1958; L. Pauling, The Nature of the Chemical Bond, 3rd Ed., Cornell University Press, Ithaca, NY. 1960.
    • (1958) The Strengths of Chemical Bonds, 2nd Ed.
    • Cottrell, T.L.1
  • 5
    • 0003438540 scopus 로고
    • Cornell University Press, Ithaca, NY.
    • T. L. Cottrell, The Strengths of Chemical Bonds, 2nd ed., Butterworths, London, 1958; L. Pauling, The Nature of the Chemical Bond, 3rd Ed., Cornell University Press, Ithaca, NY. 1960.
    • (1960) The Nature of the Chemical Bond, 3rd Ed.
    • Pauling, L.1
  • 8
    • 4244190838 scopus 로고
    • Dissertation, Technische Universität, Karlsruhe
    • b) C. Süling, Dissertation, Technische Universität, Karlsruhe, 1992.
    • (1992)
    • Süling, C.1
  • 9
    • 0344950672 scopus 로고    scopus 로고
    • 1H NMR spectroscopy (ca. -80°C). Therefore, it is plausible to assume dipolarophilic behavior of the three-membered ring ketones towards 6. The spiroozonides of the tropones fragment at -60 to + 50°C. The half-lives are informative: C. Berger, S. Dietrich, U. Dilger, D. Geuenich, H. Helios, R. Herges, P. Kirchmer, H. Röttele, G. Schröder, Angew. Chem. 1998, 110, 1954-1957; Angew. Chem. Int. Ed. 1998, 37, 1854-1856.
    • (1998) Angew. Chem. , vol.110 , pp. 1954-1957
    • Berger, C.1    Dietrich, S.2    Dilger, U.3    Geuenich, D.4    Helios, H.5    Herges, R.6    Kirchmer, P.7    Röttele, H.8    Schröder, G.9
  • 10
    • 0032479760 scopus 로고    scopus 로고
    • 1H NMR spectroscopy (ca. -80°C). Therefore, it is plausible to assume dipolarophilic behavior of the three-membered ring ketones towards 6. The spiroozonides of the tropones fragment at -60 to + 50°C. The half-lives are informative: C. Berger, S. Dietrich, U. Dilger, D. Geuenich, H. Helios, R. Herges, P. Kirchmer, H. Röttele, G. Schröder, Angew. Chem. 1998, 110, 1954-1957; Angew. Chem. Int. Ed. 1998, 37, 1854-1856.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1854-1856
  • 11
    • 0344950671 scopus 로고    scopus 로고
    • note
    • 2OD(H).
  • 12
    • 0344088654 scopus 로고    scopus 로고
    • A [3+2] cycloaddition of 6 and 7 can only be performed in solvents of low polarity
    • A [3+2] cycloaddition of 6 and 7 can only be performed in solvents of low polarity.
  • 13
    • 0345382169 scopus 로고
    • W. Sander, O. L. Chapman, Angew. Chem. 1988, 100, 402-403; Angew. Chem. Int. Ed. Engl. 1988, 27, 398-399.
    • (1988) Angew. Chem. , vol.100 , pp. 402-403
    • Sander, W.1    Chapman, O.L.2
  • 14
    • 84990101266 scopus 로고
    • W. Sander, O. L. Chapman, Angew. Chem. 1988, 100, 402-403; Angew. Chem. Int. Ed. Engl. 1988, 27, 398-399.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 398-399
  • 15
    • 0344088653 scopus 로고    scopus 로고
    • note
    • 14]methylcyclohexane at 98°C are 26 and 23 min, respectively. In the first case cyclopent-3-en-1-one is the predominant product, in the second case a complex product mixture is formed. Carbon dioxide and butadiene or hexa-1,3,5-triene could not be detected.
  • 21
    • 0345382167 scopus 로고    scopus 로고
    • note
    • A synchronous mechanism is not expected because the starting materials are not symmetrical. The trioxolane ring of the starting materials is not flat, and the bonds of the three-membered ring are not equal in length.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.