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Volumn 45, Issue 12, 1997, Pages 1961-1969

Pericyclic reaction behavior of cyclopentadienones toward acyclic conjugated dienes. [3,3]-Sigmatropic rearrangement and double diels-alder reactions of the endo[4+2]π cycloadducts

Author keywords

1,3 alkadiene; Ab initio calculation; Cyclopentadienone; Dieis Alder reaction; Double; X ray analysis; 3,3 sigmatropic rearrangement

Indexed keywords

ALKADIENE; CYCLOPENTADIENE DERIVATIVE;

EID: 0031443540     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1961     Document Type: Article
Times cited : (9)

References (34)
  • 4
    • 2642624514 scopus 로고
    • d) The primary [4 + 2]π cycloadduct of phencyclone and N-ethoxycarbonylazepine was isolated, and it underwent [3,3]-sigmatropic rearrangement to give the [2 + 4]π cycloadduct: Yasuda M., Harano K., Kanematsu K., J. Org. Chem., 45, 2368-2372 (1980).
    • (1980) J. Org. Chem. , vol.45 , pp. 2368-2372
    • Yasuda, M.1    Harano, K.2    Kanematsu, K.3
  • 10
    • 0001888675 scopus 로고
    • AM1 and PM3 calculations were performed using MOPAC ver. 6.0 (QCPE No. 445), Stewart J. J. P., QCPE Bull., 10, 86 (1990).
    • (1990) QCPE Bull. , vol.10 , pp. 86
    • Stewart, J.J.P.1
  • 12
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    • 3J) between the bridge carbonyl carbon and the exo and endo methylene protons of norbornen-7-one have been reported to be 0 and 5-9 Hz, respectively; Tan R. Y. S., Russel R. A., Warrener R. N., Tetrahedron Lett., 1979, 5031-5034.
    • Tetrahedron Lett. , vol.1979 , pp. 5031-5034
    • Tan, R.Y.S.1    Russel, R.A.2    Warrener, R.N.3
  • 14
    • 0003625321 scopus 로고
    • Ork Ridge National Laboratory, Oak Ridge, TN
    • Johnson C. K., "ORTEP, Report ORNL-3794," Ork Ridge National Laboratory, Oak Ridge, TN, 1965.
    • (1965) ORTEP, Report ORNL-3794
    • Johnson, C.K.1
  • 17
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    • The force field calculations were performed on a Scientists' Paradise Dragon AXP5A/433 computer using the Spartan 4.1 program package, Wavefunction, Inc., California, U. S. A., 1995
    • c) The force field calculations were performed on a Scientists' Paradise Dragon AXP5A/433 computer using the Spartan 4.1 program package, Wavefunction, Inc., California, U. S. A., 1995.
  • 21
    • 0001512798 scopus 로고
    • Osawa E., Ivanov P. M., Jaime C., J. Org. Chem., 48, 3990 (1983); Osawa E., Musso H., Top. Stereochem., 13, 170-171 (1982) and references cited therein.
    • (1983) J. Org. Chem. , vol.48 , pp. 3990
    • Osawa, E.1    Ivanov, P.M.2    Jaime, C.3
  • 22
    • 0001512798 scopus 로고
    • and references cited therein
    • Osawa E., Ivanov P. M., Jaime C., J. Org. Chem., 48, 3990 (1983); Osawa E., Musso H., Top. Stereochem., 13, 170-171 (1982) and references cited therein.
    • (1982) Top. Stereochem. , vol.13 , pp. 170-171
    • Osawa, E.1    Musso, H.2
  • 26
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    • a) Klopman G., J. Am. Chem. Soc., 90, 223-234 (1968); Salem L., ibid., 90, 543-552, 553-566 (1968);
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 223-234
    • Klopman, G.1
  • 27
    • 33947321923 scopus 로고
    • a) Klopman G., J. Am. Chem. Soc., 90, 223-234 (1968); Salem L., ibid., 90, 543-552, 553-566 (1968);
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 543-552
  • 28
    • 2642653133 scopus 로고    scopus 로고
    • note
    • -2 eV.
  • 29
    • 2642600957 scopus 로고    scopus 로고
    • See ref. 12b, p. 28.
    • See ref. 12b, p. 28.
  • 30


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.