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Digitale Medien

Relative rates of bromination and chlorination of 4-substituted cyclopentenes in methanol, ethanol and acetic acid (1989)

Zhang, Ben-Li ; Qiu, Jian ; Gao, Zhen-Heng

Chichester : Wiley-Blackwell

Journal of Physical Organic Chemistry 2 (1989), S. 26-34

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Details

ISSN: 0894-3230

Schlagwort(e): Organic Chemistry ; Physical Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie , Physik

Notizen: A set of 4-monosubstituted cyclopentenes, , were synthesized and their relative rates (kX/kH) for bromination and chlorination were determined in methanol, ethanol and acetic acid at 25 °C by competitive method. log(kX/kH) for most of the substituents can be correlated by means of Taft's equation, log(kX/kH) = ρI σI + C. In methanol ρI, Br2 = -2·91, ρI, Cl2 = -0·49, in ethanol ρI, Br2 = -3·07, ρI, Cl2 = -0·70 and in acetic acid ρI, Br2 = -1·64, ρI, Cl2 = -0·65. The presence of C(〈0) is due to a constant steric effect. The deviation of X = H is ascribed to the absence of the steric effect and that of X = CO2Me and CO2Et is accounted for in terms of anchimeric assistance. For chlorination no anchimeric assistance was observed.

Zusätzliches Material: 1 Ill.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/poc.610020104

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