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Volumn 68, Issue 3, 2003, Pages 1117-1127

Carbocation-forming reactions in dimethyl sulfoxide

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATION;

EID: 0037423163     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026468x     Document Type: Article
Times cited : (28)

References (48)
  • 13
    • 0347456033 scopus 로고    scopus 로고
    • note
    • 3N. See Experimental Section for details.
  • 22
    • 0347456036 scopus 로고
    • Although the exo/endo ratio of 20.x for 17 and 15 might be considered small, comparable values are seen in other 2-norbornyl systems solvolyzing via cationic mechanisms. See: Wilcox, C. F.; Jesaitis, R. G. Tetrahedron Lett. 1967, 2567. (b) Wilcox, C. F.; Jesaitis, R. G. Chem. Commun. 1967, 1056. (c) Traylor, T. G. Perrin, C. L. J. Am. Chem. Soc. 1966, 88, 4934.
    • (1967) Tetrahedron Lett. , vol.2567
    • Wilcox, C.F.1    Jesaitis, R.G.2
  • 23
    • 0348085973 scopus 로고
    • Although the exo/endo ratio of 20.x for 17 and 15 might be considered small, comparable values are seen in other 2-norbornyl systems solvolyzing via cationic mechanisms. See: Wilcox, C. F.; Jesaitis, R. G. Tetrahedron Lett. 1967, 2567. (b) Wilcox, C. F.; Jesaitis, R. G. Chem. Commun. 1967, 1056. (c) Traylor, T. G. Perrin, C. L. J. Am. Chem. Soc. 1966, 88, 4934.
    • (1967) Chem. Commun , vol.1056
    • Wilcox, C.F.1    Jesaitis, R.G.2
  • 24
    • 0000391497 scopus 로고
    • Although the exo/endo ratio of 20.x for 17 and 15 might be considered small, comparable values are seen in other 2-norbornyl systems solvolyzing via cationic mechanisms. See: Wilcox, C. F.; Jesaitis, R. G. Tetrahedron Lett. 1967, 2567. (b) Wilcox, C. F.; Jesaitis, R. G. Chem. Commun. 1967, 1056. (c)Traylor, T. G. Perrin, C. L. J. Am. Chem. Soc. 1966, 88, 4934.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4934
    • Traylor, T.G.1    Perrin, C.L.2
  • 28
    • 0348085969 scopus 로고    scopus 로고
    • note
    • Rates of reaction of 16 and 22 are extremely concentration dependent due to the common ion effect. Chloride 16 (0.0015 M) is 50% reacted in 70 min at 25 °C.
  • 30
    • 0000514362 scopus 로고
    • Protonation of norbornenes from the exo-face is well established. Microscopic reversibility requires that exo-deprotonation of norbornyl cations be much faster than endo-deprotonation. See: Kropp, P. J. J. Am. Chem. Soc. 1973, 95, 4611. (b) Stille, J. K.; Hughes, R. D. J. Org. Chem. 1971, 36, 340. (c) Brown, H. C.; Liu, K.-T. J. Am. Chem. Soc. 1975, 97, 2469. (d) Brown, H. C.; Kawakami, J. H. J. Am. Chem. Soc. 1975, 97, 5521.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4611
    • Kropp, P.J.1
  • 31
    • 0001075425 scopus 로고
    • Protonation of norbornenes from the exo-face is well established. Microscopic reversibility requires that exo-deprotonation of norbornyl cations be much faster than endo-deprotonation. See: Kropp, P. J. J. Am. Chem. Soc. 1973, 95, 4611. (b) Stille, J. K.; Hughes, R. D. J. Org. Chem. 1971, 36, 340. (c) Brown, H. C.; Liu, K.-T. J. Am. Chem. Soc. 1975, 97, 2469. (d) Brown, H. C.; Kawakami, J. H. J. Am. Chem. Soc. 1975, 97, 5521.
    • (1971) J. Org. Chem. , vol.36 , pp. 340
    • Stille, J.K.1    Hughes, R.D.2
  • 32
    • 33847802620 scopus 로고
    • Protonation of norbornenes from the exo-face is well established. Microscopic reversibility requires that exo-deprotonation of norbornyl cations be much faster than endo-deprotonation. See: Kropp, P. J. J. Am. Chem. Soc. 1973, 95, 4611. (b) Stille, J. K.; Hughes, R. D. J. Org. Chem. 1971, 36, 340. (c) Brown, H. C.; Liu, K.-T. J. Am. Chem. Soc. 1975, 97, 2469. (d) Brown, H. C.; Kawakami, J. H. J. Am. Chem. Soc. 1975, 97, 5521.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2469
    • Brown, H.C.1    Liu, K.-T.2
  • 33
    • 0348085971 scopus 로고
    • Protonation of norbornenes from the exo-face is well established. Microscopic reversibility requires that exo-deprotonation of norbornyl cations be much faster than endo-deprotonation. See: Kropp, P. J. J. Am. Chem. Soc. 1973, 95, 4611. (b) Stille, J. K.; Hughes, R. D. J. Org. Chem. 1971, 36, 340. (c) Brown, H. C.; Liu, K.-T. J. Am. Chem. Soc. 1975, 97, 2469. (d) Brown, H. C.; Kawakami, J. H. J. Am. Chem. Soc. 1975, 97, 5521.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 5521
    • Brown, H.C.1    Kawakami, J.H.2
  • 40
    • 0034630905 scopus 로고    scopus 로고
    • + has been spectroscopically characterized at low temperatures. See: Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4269
    • Garcia, B.A.1    Gin, D.Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.