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Volumn 63, Issue 24, 1998, Pages 8624-8625

Unexpected cis,cis to trans,trans isomerization of a disilanyl analogue of 1,5-cyclooctadiene

Author keywords

[No Author keywords available]

Indexed keywords

1,5 CYCLOOCTADIENE; ALKADIENE; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 0031766530     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981213y     Document Type: Article
Times cited : (3)

References (22)
  • 1
    • 33845552545 scopus 로고
    • Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 105, 3359. Gleiter, R.; Schafer, W.; Sakurai, H. J. Am. Chem. Soc. 1983,105, 3046. Iwahara, T.; West, R. J. Chem. Soc., Chem. Commun. 1988, 954. Ishikawa, M.; Hatano, T.; Hasegawa, Y.; Horio, T.; Funai, A.; Miyai, A; Ishita, T.; Tsukihara, T.; Yamanaka, T.; Koike, T.; Shioya, J. Organometallics 1992, 11, 1604. Sakurai, H.; Tominaga, K; Watanabe, K.; Kumada, M. Tetrahedron Lett. 1966, 45, 5493.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3359
    • Sakurai, H.1    Nakadaira, Y.2    Hosomi, A.3    Eriyama, Y.4    Kabuto, C.5
  • 2
    • 33845552545 scopus 로고
    • Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 105, 3359. Gleiter, R.; Schafer, W.; Sakurai, H. J. Am. Chem. Soc. 1983,105, 3046. Iwahara, T.; West, R. J. Chem. Soc., Chem. Commun. 1988, 954. Ishikawa, M.; Hatano, T.; Hasegawa, Y.; Horio, T.; Funai, A.; Miyai, A; Ishita, T.; Tsukihara, T.; Yamanaka, T.; Koike, T.; Shioya, J. Organometallics 1992, 11, 1604. Sakurai, H.; Tominaga, K; Watanabe, K.; Kumada, M. Tetrahedron Lett. 1966, 45, 5493.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 3046
    • Gleiter, R.1    Schafer, W.2    Sakurai, H.3
  • 3
    • 37049081160 scopus 로고
    • Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 105, 3359. Gleiter, R.; Schafer, W.; Sakurai, H. J. Am. Chem. Soc. 1983,105, 3046. Iwahara, T.; West, R. J. Chem. Soc., Chem. Commun. 1988, 954. Ishikawa, M.; Hatano, T.; Hasegawa, Y.; Horio, T.; Funai, A.; Miyai, A; Ishita, T.; Tsukihara, T.; Yamanaka, T.; Koike, T.; Shioya, J. Organometallics 1992, 11, 1604. Sakurai, H.; Tominaga, K; Watanabe, K.; Kumada, M. Tetrahedron Lett. 1966, 45, 5493.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 954
    • Iwahara, T.1    West, R.2
  • 4
    • 20944447964 scopus 로고
    • Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 105, 3359. Gleiter, R.; Schafer, W.; Sakurai, H. J. Am. Chem. Soc. 1983,105, 3046. Iwahara, T.; West, R. J. Chem. Soc., Chem. Commun. 1988, 954. Ishikawa, M.; Hatano, T.; Hasegawa, Y.; Horio, T.; Funai, A.; Miyai, A; Ishita, T.; Tsukihara, T.; Yamanaka, T.; Koike, T.; Shioya, J. Organometallics 1992, 11, 1604. Sakurai, H.; Tominaga, K; Watanabe, K.; Kumada, M. Tetrahedron Lett. 1966, 45, 5493.
    • (1992) Organometallics , vol.11 , pp. 1604
    • Ishikawa, M.1    Hatano, T.2    Hasegawa, Y.3    Horio, T.4    Funai, A.5    Miyai, A.6    Ishita, T.7    Tsukihara, T.8    Yamanaka, T.9    Koike, T.10    Shioya, J.11
  • 5
    • 0041505406 scopus 로고
    • Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Kabuto, C. J. Am. Chem. Soc. 1983, 105, 3359. Gleiter, R.; Schafer, W.; Sakurai, H. J. Am. Chem. Soc. 1983,105, 3046. Iwahara, T.; West, R. J. Chem. Soc., Chem. Commun. 1988, 954. Ishikawa, M.; Hatano, T.; Hasegawa, Y.; Horio, T.; Funai, A.; Miyai, A; Ishita, T.; Tsukihara, T.; Yamanaka, T.; Koike, T.; Shioya, J. Organometallics 1992, 11, 1604. Sakurai, H.; Tominaga, K; Watanabe, K.; Kumada, M. Tetrahedron Lett. 1966, 45, 5493.
    • (1966) Tetrahedron Lett. , vol.45 , pp. 5493
    • Sakurai, H.1    Tominaga, K.2    Watanabe, K.3    Kumada, M.4
  • 8
    • 15444358922 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy, we have found that 2 is more labile than 1 under the isomerization conditions. Further-more, at the latter stages of the isomerization, the rate of loss of 2 becomes competitive with the rate of isomerization of 1 to 2. Consequently, we feel that the inability to detect trace amounts of 1 in the attempted isomerization of 2 to 1 provides strong (albeit negative) evidence that 2 is thermodynamically more stable than 1 within the limits described in the text.
  • 14
    • 15444355116 scopus 로고    scopus 로고
    • note
    • 11,12 In all cases, optimal geometries were determined without the use of additional symmetrization of the Hamiltonian (NOSYMTRY option). The absence of imaginary normal-mode frequencies confirmed that the structures correspond to local energy minima.
  • 15
    • 0003422019 scopus 로고    scopus 로고
    • Wavefunction, Inc., Irvine, CA
    • Spartan version 5.0, Wavefunction, Inc., Irvine, CA 1997.
    • (1997) Spartan Version 5.0
  • 17
    • 15444348170 scopus 로고    scopus 로고
    • note
    • We note that minimization with the PM3 Hamiltonian appears to provide the closest qualitative resemblance to the X-ray structures of 1 and 2 in terms of bond lengths and angles.
  • 18


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.