ChemInform Abstract: Substituent Effects in the Solvolysis of p-(2-Substituted Cyclopropyl)- α-Methylbenzyl Chlorides

Autor: Tamami Kagosaku, Takako Kubo, Kenjiro Tokami, Yoshiaki Kusuyama, Masami Iyo
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 23
ISSN: 0931-7597
Popis: The solvolysis rates of p-(cis- or trans-2-substituted cyclopropyl)-α-methylbenzyl chlorides including electron-donating and electron-attracting substituents relative to a hydrogen substituent were measured in 80% aqueous acetone. The trans isomers were more reactive than the corresponding cis derivatives where cyclopropyl and phenyl groups could not get a most favorable “bisected” conformation for the cyclopropyl group to release electrons to the benzene ring. The relative rates of the trans isomers at 45°C were best correlated by means of σm values with a ρ value of −3.14 and a correlation coefficient of 0.97, indicating that the cyclopropane ring was a poor transmitter of a resonance effect. The substituent effects were analyzed by means of the LSFE equation.
Databáze: OpenAIRE