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Volumn 121, Issue 50, 1999, Pages 11885-11893

Isotope effects and the mechanism of triazolinedione ene reactions. Aziridinium imides are innocent bystanders

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; CARBON 13; DEUTERIUM; IMIDE; TRIAZOLINE DERIVATIVE;

EID: 0033596296     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9933339     Document Type: Article
Times cited : (59)

References (49)
  • 1
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    • Frimer, A. A., Ed.; CRC Press: Boca Raton, FL
    • 2; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; pp 68-87.
    • (1985) 2 , pp. 68-87
    • Frimer, A.A.1    Stephenson, L.M.2
  • 6
    • 0009467422 scopus 로고
    • Achmatowicz, O., Jr.; Szymoniak, J. J. Org. Chem. 1980, 45, 4774. Kwart, H.; Brechbiel, M. W. J. Org. Chem. 1982, 47, 3355. Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3953.
    • (1980) J. Org. Chem. , vol.45 , pp. 4774
    • Achmatowicz O., Jr.1    Szymoniak, J.2
  • 7
    • 0009467422 scopus 로고
    • Achmatowicz, O., Jr.; Szymoniak, J. J. Org. Chem. 1980, 45, 4774. Kwart, H.; Brechbiel, M. W. J. Org. Chem. 1982, 47, 3355. Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3953.
    • (1982) J. Org. Chem. , vol.47 , pp. 3355
    • Kwart, H.1    Brechbiel, M.W.2
  • 8
    • 0001120647 scopus 로고
    • Achmatowicz, O., Jr.; Szymoniak, J. J. Org. Chem. 1980, 45, 4774. Kwart, H.; Brechbiel, M. W. J. Org. Chem. 1982, 47, 3355. Dai, S.-H.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1972, 94, 3953.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3953
    • Dai, S.-H.1    Dolbier W.R., Jr.2
  • 24
    • 0343228454 scopus 로고    scopus 로고
    • note
    • 13C NMR which prevented the accurate integration of C5.
  • 25
    • 0342358880 scopus 로고    scopus 로고
    • note
    • A fourth regioisomeric transition structure in which N2 is anti to C4 was higher in energy (5.4 kcal/mol at the Becke3LYP level) and was not considered further.
  • 28
    • 0024841752 scopus 로고
    • with Becke3LYP frequencies scaled by 0.9614
    • The calculations used the program QUIVER (Saunders. M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP frequencies scaled by 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8989
    • Saunders, M.1    Laidig, K.E.2    Wolfsberg, M.3
  • 29
    • 0011083273 scopus 로고    scopus 로고
    • The calculations used the program QUIVER (Saunders. M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989) with Becke3LYP frequencies scaled by 0.9614 (Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502).
    • (1996) J. Phys. Chem. , vol.100 , pp. 16502
    • Scott, A.P.1    Radom, L.2
  • 38
    • 0342793906 scopus 로고    scopus 로고
    • note
    • D.
  • 48
    • 0029964954 scopus 로고    scopus 로고
    • 2 (using data from ref 33) shows no significant curvature. Therefore tunneling in the formation of the ene product is unlikely to account for the large curvature seen in Figure 5
    • 2 (using data from ref 33) shows no significant curvature. Therefore tunneling in the formation of the ene product is unlikely to account for the large curvature seen in Figure 5.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10319
    • Jonsson, T.1    Glickman, M.H.2    Sun, S.3    Klinman, J.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.