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Volumn 127, Issue 51, 2005, Pages 18107-18113

Pressure independence of stereomutation and fragmentation in the bis-spirocyclobutanes, anti- and syn-2,9-dicyanodispiro[5.0.5.2]tetradeca-1,8- dienes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; RATE CONSTANTS; SENSITIVITY ANALYSIS; STEREOCHEMISTRY;

EID: 29844441764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053168z     Document Type: Article
Times cited : (5)

References (26)
  • 2
    • 31144435950 scopus 로고    scopus 로고
    • published online Sept. 2
    • Northrop, B. H.; Houk, K. N. J. Org. Chem., published online Sept. 2, 2005 http://dx.doi.org/10.1021/jo051273L.
    • (2005) J. Org. Chem.
    • Northrop, B.H.1    Houk, K.N.2
  • 11
    • 29844432649 scopus 로고    scopus 로고
    • note
    • -1). As a second, note that the two cyclohexenes of the first, highly likely concerted, constitutionally Diels-Alder set would have involved the less well stabilized diradicals had they been involved, whereas the not obviously concerted constitutionally Diels-Alder cyclohexene of the second set is derived, as are the two cyclobutanes, from the optimally stabilized racemic and meso diradicals.
  • 14
    • 10944272485 scopus 로고    scopus 로고
    • and references therein
    • See also: Hoffmann, R. Angew. Chem., Int. Ed. 2004, 43, 6586-6590 and references therein.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 6586-6590
    • Hoffmann, R.1
  • 17
    • 0003512432 scopus 로고
    • note
    • In the case of the [2+2] cycloaddition of 1,1-difluoroallene, there is good evidence that the ratio of products derived from a diradical intermediate can indeed be pressure-dependent. At high pressure the product resulting from ring closure in the diradical intermediate is favored over that resulting from bond rotation followed by ring closure. Dolbier, W. R., Jr.; Weaver, S. L. J. Org. Chem. 1990, 55, 711-715.
    • (1990) J. Org. Chem. , vol.55 , pp. 711-715
    • Dolbier Jr., W.R.1    Weaver, S.L.2
  • 22
    • 29844450699 scopus 로고    scopus 로고
    • note
    • -1, respectively (standard errors!). Recalculation affords somewhat altered values for the energies of activation that emphasize the poorer quality of the data relating to syn-2: anti-2 → syn-2, 31.4 ± 1.1; syn-2 → anti-2, 34.2 ± 8.2; anti-2 → 1 (methylenecyclohexene), 33.0 ± 1.9; syn-2 → 1, 30.3 ± 6.4 (95% confidence level).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.