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Volumn 63, Issue 21, 1998, Pages 7425-7436

Ab initio study of the regiochemistry of 1,3-dipolar cycloadditions. Reactions of diazomethane and formonitrile oxide with ethene, propene, acrylonitrile, and methyl vinyl ether

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Indexed keywords


EID: 84962376558     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9812633     Document Type: Article
Times cited : (55)

References (70)
  • 1
    • 0004101860 scopus 로고
    • Padwa, A., Ed.; Wiley-Interscience: New York
    • 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vols. 1-2.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1-2
  • 5
    • 0001783677 scopus 로고
    • Steric Course and Mechanism of 1,3-Dipolar cycloaddition
    • Curran, D. P., Ed.; JAI Press: London
    • Huisgen, R. Steric Course and Mechanism of 1,3-Dipolar cycloaddition. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, 1988; Vol. 1.
    • (1988) Advances in Cycloaddition , vol.1
    • Huisgen, R.1
  • 7
    • 84962421632 scopus 로고    scopus 로고
    • Reference 3d, pp 28, 29
    • (e) Reference 3d, pp 28, 29.
  • 8
    • 84962421623 scopus 로고    scopus 로고
    • Reference 3d, pp 95-97
    • (f) Reference 3d, pp 95-97.
  • 9
    • 84962421624 scopus 로고    scopus 로고
    • Reference 3d, pp 81-87
    • (g) Reference 3d, pp 81-87.
  • 22
    • 84962422482 scopus 로고    scopus 로고
    • p 153
    • (b) p 153.
  • 25
    • 0000994006 scopus 로고
    • Theory of 1,3-Dipolar Cycloadditions
    • Padwa, A., Ed.; Wiley: New York
    • Houk, K. N. Theory of 1,3-Dipolar Cycloadditions. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, p 442.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.2 , pp. 442
    • Houk, K.N.1
  • 47
    • 84962365568 scopus 로고    scopus 로고
    • note
    • -1 in solution with dielectric constants of 2.23, 4.9, and 38.2, respectively.
  • 49
    • 84962365541 scopus 로고    scopus 로고
    • note
    • Unfortunately, in a previous paper of ours (ref 15, Table 1) formonitrile oxide was given incorrect values of ZPE, δH, S, δG, and in particular, a definitely lower value for the standard entropy (41.81 instead of 53.26 eu). There we concluded that for formonitrile oxide cycloadditions "the calculated absolute value of the negative activation entropy is probably significantly underestimated (by, at least, 10 eu) with respect to the experimental values ...". Now, we observe that the disagreement between theory and experiment disappears when the correct values are used.
  • 61
    • 84962458022 scopus 로고    scopus 로고
    • note
    • methyl acrylate = 0.20 ± 0.01).
  • 70
    • 84962458012 scopus 로고    scopus 로고
    • We showed in ref 11 that the complete charge-transfer term between MVEsyn and DZM, at variance with the simple frontier interaction, points to a mixture of adducts
    • We showed in ref 11 that the complete charge-transfer term between MVEsyn and DZM, at variance with the simple frontier interaction, points to a mixture of adducts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.