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Volumn 38, Issue 38, 1997, Pages 6693-6696

A cyclopropyl group shows reverse facial selectivity depending on the bicyclic ring system

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[2.2.2]OCTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; NORBORNANE DERIVATIVE;

EID: 0030794917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01567-0     Document Type: Article
Times cited : (9)

References (36)
  • 10
    • 0343163725 scopus 로고
    • f)
    • f) Geibel, K., Chem. Ber. 1970, 103, 1637-1644.
    • (1970) Chem. Ber. , vol.103 , pp. 1637-1644
    • Geibel, K.1
  • 12
    • 84984238676 scopus 로고
    • Calculated geometries of 5a and 6a, optimized with HF/6-31G* basis sets, show that both compounds exhibit tilting of the olefin plane toward the ethano bridge bearing the cyclopropyl group (data not shown). These geometrical perturbations do not appear to determine the facial selectivity of 5a and 6a, because the reverse facial preference was observed. An X-ray determination of the related aziridine derivative of 7-methylidenenorbornane was previously reported
    • Calculated geometries of 5a and 6a, optimized with HF/6-31G* basis sets, show that both compounds exhibit tilting of the olefin plane toward the ethano bridge bearing the cyclopropyl group (data not shown). These geometrical perturbations do not appear to determine the facial selectivity of 5a and 6a, because the reverse facial preference was observed. An X-ray determination of the related aziridine derivative of 7-methylidenenorbornane was previously reported: Maasa, W.; Birkhahn, M.; Landmann, B.; Hoffmann, R.W. Chem. Ber., 1983, 116, 404-408. See also Laube, T., J. Am. Chem. Soc. 1989, 111, 9224-9232.
    • (1983) Chem. Ber. , vol.116 , pp. 404-408
    • Maasa, W.1    Birkhahn, M.2    Landmann, B.3    Hoffmann, R.W.4
  • 13
    • 0024848879 scopus 로고
    • See also
    • Calculated geometries of 5a and 6a, optimized with HF/6-31G* basis sets, show that both compounds exhibit tilting of the olefin plane toward the ethano bridge bearing the cyclopropyl group (data not shown). These geometrical perturbations do not appear to determine the facial selectivity of 5a and 6a, because the reverse facial preference was observed. An X-ray determination of the related aziridine derivative of 7-methylidenenorbornane was previously reported: Maasa, W.; Birkhahn, M.; Landmann, B.; Hoffmann, R.W. Chem. Ber., 1983, 116, 404-408. See also Laube, T., J. Am. Chem. Soc. 1989, 111, 9224-9232.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9224-9232
    • Laube, T.1
  • 14
    • 0343163720 scopus 로고    scopus 로고
    • The configurations of the diol (or epoxide) moieties were elucidated on the basis of the characteristic anisotropy effects of the diols (or the epoxide) and the cyclopropyl group (see c and ). The structures of the some of the major products (syn-diols of 5a and 5c, and syn-epoxide of 5d) were also confirmed by X-ray crystallographic analysis. The structures of the diol of 6a were also elucidated on the basis of the NOE enhancement.
    • The configurations of the diol (or epoxide) moieties were elucidated on the basis of the characteristic anisotropy effects of the diols (or the epoxide) and the cyclopropyl group (see c and ). The structures of the some of the major products (syn-diols of 5a and 5c, and syn-epoxide of 5d) were also confirmed by X-ray crystallographic analysis. The structures of the diol of 6a were also elucidated on the basis of the NOE enhancement.
  • 20
    • 84980187522 scopus 로고
    • 5b was prepared by Diels-Alder cycloaddition, like 5a, as described by followed by olefin formation as described in
    • 5b was prepared by Diels-Alder cycloaddition, like 5a, as described by Musso, H., Chem. Ber., 1975, 108, 337-356, followed by olefin formation as described in .
    • (1975) Chem. Ber. , vol.108 , pp. 337-356
    • Musso, H.1
  • 34
    • 0342294022 scopus 로고    scopus 로고
    • The energy level of the Walsh orbital (NXHOMO) of cyanocyclopropane is lower than that of unsubstituted cyclopropane. The cyano group also redistributes the orbital coefficients, leading to a reduction of the orbital coefficient of the cyclopropane moiety in the relevant Walsh orbital
    • The energy level of the Walsh orbital (NXHOMO) of cyanocyclopropane is lower than that of unsubstituted cyclopropane. The cyano group also redistributes the orbital coefficients, leading to a reduction of the orbital coefficient of the cyclopropane moiety in the relevant Walsh orbital.
  • 35
    • 0010667157 scopus 로고
    • A cyclopropyl group showed the divergent anisotropy effect, i.e., deshielding or shielding, depending on the conformation
    • A cyclopropyl group showed the divergent anisotropy effect, i.e., deshielding or shielding, depending on the conformation: Christl, M. Chem. Ber., 1975, 108, 2781-2791.; Christl, M.; Herbert, R., Chem. Ber., 1979, 112, 2022-2027. and d. The rigid structures such as 5a and 6a exclude the possible conformational effect of the cyclopropyl group.
    • (1975) Chem. Ber. , vol.108 , pp. 2781-2791
    • Christl, M.1
  • 36
    • 84982074918 scopus 로고
    • and d. The rigid structures such as 5a and 6a exclude the possible conformational effect of the cyclopropyl group
    • A cyclopropyl group showed the divergent anisotropy effect, i.e., deshielding or shielding, depending on the conformation: Christl, M. Chem. Ber., 1975, 108, 2781-2791.; Christl, M.; Herbert, R., Chem. Ber., 1979, 112, 2022-2027. and d. The rigid structures such as 5a and 6a exclude the possible conformational effect of the cyclopropyl group.
    • (1979) Chem. Ber. , vol.112 , pp. 2022-2027
    • Christl, M.1    Herbert, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.