메뉴 건너뛰기




Volumn 119, Issue 35, 1997, Pages 8201-8208

Radical ion probes. 6. Origin of the high intrinsic barrier to nucleophile-induced ring opening of arylcyclopropane radical cations

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; NAPHTHALENE DERIVATIVE; RADICAL;

EID: 0030822160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970932b     Document Type: Article
Times cited : (20)

References (47)
  • 5
    • 0000897453 scopus 로고
    • Silverman, R. B.; Hoffman, S. J. J. Am. Chem. Soc. 1980, 102, 884. Silverman, R. B.; Hoffman, S. J.; Catus, W. B., III. J. Am. Chem. Soc. 1980, 102, 7126.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 884
    • Silverman, R.B.1    Hoffman, S.J.2
  • 8
    • 0000414379 scopus 로고
    • Hanzlik, R. P.; Tullman, R. H. J. Am. Chem. Soc. 1982, 104, 2048. Riley, P.; Hanzlik, R. P. Tetrahedron Lett. 1989, 30, 3015.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3015
    • Riley, P.1    Hanzlik, R.P.2
  • 12
    • 0000415867 scopus 로고
    • This bimolecular mechanism for cyclopropane ring opening was originally proposed by Rao and Hixson. See: Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6458
    • Rao, V.R.1    Hixson, S.S.2
  • 17
    • 0011492020 scopus 로고
    • 3OH generally leads to ring-opened products, i.e., the corresponding 1,3-dimethoxypropylarenes. See: Shono, T.; Matsumura, Y. J. Org. Chem. 1970, 35, 4157.
    • (1970) J. Org. Chem. , vol.35 , pp. 4157
    • Shono, T.1    Matsumura, Y.2
  • 18
    • 0008848909 scopus 로고
    • Nadjo, L.; Savéant, J. M. Electroanal. Chem. 1973, 48, 113. Andrieux, C. P.; Savéant, J. M. In Investigation of Rates and Mechanisms of Reactions, 4th ed.; Bernasconi, C., Ed.; Wiley: New York, 1986; Part II, pp 305-390.
    • (1973) Electroanal. Chem. , vol.48 , pp. 113
    • Nadjo, L.1    Savéant, J.M.2
  • 20
    • 77956807190 scopus 로고
    • Fry, A. J., Britton, W., Eds.; Plenum Press: New York
    • Parker, V. D. In Topics in Organic Electrochemistry; Fry, A. J., Britton, W., Eds.; Plenum Press: New York, 1986; pp 35-79. Parker, V. D. In Comprehensive Chemical Kinetics, Vol. 26, Electrode Kinetics: Principles and Methodology; Bamford, C. H., Compton, R. G., Eds.; Elsevier: New York, 1986; pp 145-202.
    • (1986) Topics in Organic Electrochemistry , pp. 35-79
    • Parker, V.D.1
  • 21
    • 77956807190 scopus 로고
    • Bamford, C. H., Compton, R. G., Eds.; Elsevier: New York
    • Parker, V. D. In Topics in Organic Electrochemistry; Fry, A. J., Britton, W., Eds.; Plenum Press: New York, 1986; pp 35-79. Parker, V. D. In Comprehensive Chemical Kinetics, Vol. 26, Electrode Kinetics: Principles and Methodology; Bamford, C. H., Compton, R. G., Eds.; Elsevier: New York, 1986; pp 145-202.
    • (1986) Comprehensive Chemical Kinetics, Vol. 26, Electrode Kinetics: Principles and Methodology , vol.26 , pp. 145-202
    • Parker, V.D.1
  • 22
    • 1842410593 scopus 로고    scopus 로고
    • 2•+]. However, only the former is consistent with the LSV results
    • 2•+]. However, only the former is consistent with the LSV results.
  • 23
    • 1842291998 scopus 로고    scopus 로고
    • Simulations were performed using DigiSim 2.1 (R)
    • distributed by Bioanalytical Systems Inc., 2701 Kent Ave. West Lafayette, IN 47906
    • Simulations were performed using DigiSim 2.1 (R) - A General Simulation Program for Cyclic Voltammetry, Rudolph M.; Feldberg, S. W., distributed by Bioanalytical Systems Inc., 2701 Kent Ave. West Lafayette, IN 47906.
    • A General Simulation Program for Cyclic Voltammetry
    • Rudolph, M.1    Feldberg, S.W.2
  • 24
    • 37049078442 scopus 로고
    • For a recent discussion of the dehydrodimerization of naphthalene radical cations to form binaphthyls, see: Eberson, L.; Hartshorn, M. P.; Persson, O. J. Chem. Soc., Perkin Trans. 2 1995, 409. See also: Butts, C. P.; Eberson, L.; Hartshorn, M. P.; Persson, O.; Robinson, W. T. Acta Chem. Scand. 1995, 49, 253.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 409
    • Eberson, L.1    Hartshorn, M.P.2    Persson, O.3
  • 25
    • 0343869778 scopus 로고
    • For a recent discussion of the dehydrodimerization of naphthalene radical cations to form binaphthyls, see: Eberson, L.; Hartshorn, M. P.; Persson, O. J. Chem. Soc., Perkin Trans. 2 1995, 409. See also: Butts, C. P.; Eberson, L.; Hartshorn, M. P.; Persson, O.; Robinson, W. T. Acta Chem. Scand. 1995, 49, 253.
    • (1995) Acta Chem. Scand. , vol.49 , pp. 253
    • Butts, C.P.1    Eberson, L.2    Hartshorn, M.P.3    Persson, O.4    Robinson, W.T.5
  • 26
    • 0001312964 scopus 로고
    • Bard, A. J., Ed.; Marcel Dekker: New York
    • Peover, M. E. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1967; pp 1-48. Phelps, J.; Santhanam, K. S. V.; Bard, A. J. J. Am. Chem. Soc. 1967, 89, 1752.
    • (1967) Electroanalytical Chemistry , pp. 1-48
    • Peover, M.E.1
  • 27
    • 0000460087 scopus 로고
    • Peover, M. E. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1967; pp 1-48. Phelps, J.; Santhanam, K. S. V.; Bard, A. J. J. Am. Chem. Soc. 1967, 89, 1752.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1752
    • Phelps, J.1    Santhanam, K.S.V.2    Bard, A.J.3
  • 28
    • 1842412350 scopus 로고    scopus 로고
    • note
    • + = 0.15, vs 0.0 for H.
  • 36
    • 0029912598 scopus 로고    scopus 로고
    • For a related discussion pertaining to reactions of nucleophiles with vinylcyclopropane radical cations, see: Herbertz, T.; Roth, H. D. J. Am. Chem. Soc. 1996, 118, 10954.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10954
    • Herbertz, T.1    Roth, H.D.2
  • 47
    • 1842371350 scopus 로고    scopus 로고
    • 4/Fe(dust)
    • 4/Fe(dust).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.