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Volumn 10, Issue 1-2, 1998, Pages 147-153

Synthesis, structure, and chiroptical properties of the first 4- oxa[7]paracyclophane

Author keywords

[No Author keywords available]

Indexed keywords

PARACYCLOPHANE DERIVATIVE; SULFONE;

EID: 0031881716     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.23     Document Type: Article
Times cited : (8)

References (41)
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    • Liebman, J.F., Greenberg, A. Chem. Rev. 76:311, 1976; de Meijere, A. Blechert, S., eds. Strain and Its Implications in Organic Chemistry. NATO ASI Series C, Vol. 273, Dordrecht: Kluwer Academic Publishers, 1988: Greenberg, A., Liebman, J.F. In: Strained Organic Molecules, Vol. 38. Wassermann, H.H., ed. New York: Academic Press, 1978:85; Olah, G.A., ed. Cage Hydrocarbons. New York: Wiley, 1989.
    • (1976) Chem. Rev. , vol.76 , pp. 311
    • Liebman, J.F.1    Greenberg, A.2
  • 2
    • 0003810689 scopus 로고
    • Strain and Its Implications in Organic Chemistry
    • Dordrecht: Kluwer Academic Publishers
    • Liebman, J.F., Greenberg, A. Chem. Rev. 76:311, 1976; de Meijere, A. Blechert, S., eds. Strain and Its Implications in Organic Chemistry. NATO ASI Series C, Vol. 273, Dordrecht: Kluwer Academic Publishers, 1988: Greenberg, A., Liebman, J.F. In: Strained Organic Molecules, Vol. 38. Wassermann, H.H., ed. New York: Academic Press, 1978:85; Olah, G.A., ed. Cage Hydrocarbons. New York: Wiley, 1989.
    • (1988) NATO ASI Series C , vol.273
    • De Meijere, A.1    Blechert, S.2
  • 3
    • 2642654763 scopus 로고
    • Wassermann, H.H., ed. New York: Academic Press
    • Liebman, J.F., Greenberg, A. Chem. Rev. 76:311, 1976; de Meijere, A. Blechert, S., eds. Strain and Its Implications in Organic Chemistry. NATO ASI Series C, Vol. 273, Dordrecht: Kluwer Academic Publishers, 1988: Greenberg, A., Liebman, J.F. In: Strained Organic Molecules, Vol. 38. Wassermann, H.H., ed. New York: Academic Press, 1978:85; Olah, G.A., ed. Cage Hydrocarbons. New York: Wiley, 1989.
    • (1978) Strained Organic Molecules , vol.38 , pp. 85
    • Greenberg, A.1    Liebman, J.F.2
  • 4
    • 0004189662 scopus 로고
    • New York: Wiley
    • Liebman, J.F., Greenberg, A. Chem. Rev. 76:311, 1976; de Meijere, A. Blechert, S., eds. Strain and Its Implications in Organic Chemistry. NATO ASI Series C, Vol. 273, Dordrecht: Kluwer Academic Publishers, 1988: Greenberg, A., Liebman, J.F. In: Strained Organic Molecules, Vol. 38. Wassermann, H.H., ed. New York: Academic Press, 1978:85; Olah, G.A., ed. Cage Hydrocarbons. New York: Wiley, 1989.
    • (1989) Cage Hydrocarbons
    • Olah, G.A.1
  • 13
    • 85085845323 scopus 로고    scopus 로고
    • note
    • 31).
  • 21
    • 0002757357 scopus 로고
    • Dohm, J., Vögtle, F. Top. Curr. Chem. 161:69, 1992. S. Laufenberg, N. Feuerbacher, I. Pischel, O. Börsch, M. Nieger, F. Vögtle, Liebigs Ann./Recueil 1997, 1901-1906.
    • (1992) Top. Curr. Chem. , vol.161 , pp. 69
    • Dohm, J.1    Vögtle, F.2
  • 24
    • 2642589522 scopus 로고    scopus 로고
    • Density functional calculations with extended TZP basis sets which include to some extent electron correlation effects show that [n]paracyclophane geometries are rather insensitive to the theoretical treatment employed. Grimme. S. Habilitation Thesis, University of Bonn, 1996
    • Density functional calculations with extended TZP basis sets which include to some extent electron correlation effects show that [n]paracyclophane geometries are rather insensitive to the theoretical treatment employed. Grimme. S. Habilitation Thesis, University of Bonn, 1996.
  • 27
    • 4243402296 scopus 로고
    • Ahlrichs, R., Bär, M., Häser, M., Horn, H., Kölmel, C. Chem. Phys. Lett. 162:165, 1989; Treutler, O., Ahlrichs, R. J. Chem. Phys. 102.346, 1995.
    • (1995) J. Chem. Phys. , vol.102 , pp. 346
    • Treutler, O.1    Ahlrichs, R.2
  • 30
    • 2642634261 scopus 로고    scopus 로고
    • note
    • α is defined as the angle between C8, the midpoint of C9/C13, and the midpoint of C10/C12. β is defined as the angle between C7, C8 and the midpoint between C9/C13.
  • 31
    • 2642689157 scopus 로고    scopus 로고
    • The COC bond angle of di-n-propylether as an unstrained reference compound is 118.0° (HF-SCF/SV), i.e. only 1.9° larger than in 3
    • The COC bond angle of di-n-propylether as an unstrained reference compound is 118.0° (HF-SCF/SV), i.e. only 1.9° larger than in 3.
  • 34
    • 2642697329 scopus 로고    scopus 로고
    • note
    • The molecules are divided into two parts with saturation of the free valencies by hydrogen or methyl groups. For the aromatic system, 1,2,4,5-tetramethylbenzene is used as a reference compound. For the chains di-n-propylether and n-heptane, respectivey, are employed as reference systems. The partial strain energies are then obtained as the energy difference of the reference molecules in the geometries of the optimized cyclophane structures and the completely relaxed systems.
  • 38
    • 85085844870 scopus 로고    scopus 로고
    • note
    • 2·dmol-1 has been calculated for 3 from the DFT/SCI data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.