An experimental and computational study about the effect of a spirocyclopropane group on the solvolysis rates of bridgehead triflates

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5611-5619

  Martínez, Antonio García ^a   Vilar, Enrique Teso ^b   De La Moya Cerero, Santiago ^a   Barcina, José Osío ^a   Gómez, Pedro C ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CATION; CYCLOPROPANE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TEMPERATURE;

EID: 0000496864     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990701i     Document Type: Article

References (89)

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32. 15b reactions involving 1-norbornyl cations, see: (a) Ebisu, K.; Batty, L. B.; Higaki, J. M.; Larson, H. O. J. Am. Chem. Soc. 1965, 87, 1400. (b) Nickon, A.; Nishida, T.; Frank, J. J. Org. Chem. 1971, 36, 1075. (c) White, E. H.; Ryan, T. J.; Field, K. W. J. Am. Chem. Soc. 1972, 94, 1360. (d) Heublein, G.; Rang, D. D. Tetrahedron 1972, 28, 1873. (e) White, E. H.; McGirk, R. H.; Aufdermarsch, C. A.; Tiwari, H. P.; Todd, M. J. J. Am. Chem. Soc. 1973, 95, 8107. (f) McKinley, J. W.; Pincock, R. E.; Scott, W. B. J. Am. Chem. Soc. 1973, 95, 2030. (g) Kirmse, W.; Schnurr, O.; Jendraller, H. Chem. Ber. 1979, 112, 2120. (h) Feldmann, G.; Kirmse, W. Angew. Chem., Int. Ed. Engl. 1987, 26, 1873. (i) Müller, P.; Milín, D.; Feng, W. O.; Houriet, R.; Della, E. W. J. Am. Chem. Soc. 1992, 114, 6169.
33. 15b reactions involving 1-norbornyl cations, see: (a) Ebisu, K.; Batty, L. B.; Higaki, J. M.; Larson, H. O. J. Am. Chem. Soc. 1965, 87, 1400. (b) Nickon, A.; Nishida, T.; Frank, J. J. Org. Chem. 1971, 36, 1075. (c) White, E. H.; Ryan, T. J.; Field, K. W. J. Am. Chem. Soc. 1972, 94, 1360. (d) Heublein, G.; Rang, D. D. Tetrahedron 1972, 28, 1873. (e) White, E. H.; McGirk, R. H.; Aufdermarsch, C. A.; Tiwari, H. P.; Todd, M. J. J. Am. Chem. Soc. 1973, 95, 8107. (f) McKinley, J. W.; Pincock, R. E.; Scott, W. B. J. Am. Chem. Soc. 1973, 95, 2030. (g) Kirmse, W.; Schnurr, O.; Jendraller, H. Chem. Ber. 1979, 112, 2120. (h) Feldmann, G.; Kirmse, W. Angew. Chem., Int. Ed. Engl. 1987, 26, 1873. (i) Müller, P.; Milín, D.; Feng, W. O.; Houriet, R.; Della, E. W. J. Am. Chem. Soc. 1992, 114, 6169.
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