V. S. Aksenov, G. A. Terent'eva
Jun 1, 1978
Citations
0
Influential Citations
2
Citations
Journal
Russian Chemical Bulletin
Abstract
1. The reaction of 1-fluoro-1-bromo-2-arylcyclopropanes with methanol occurs predominately with retention of the three -membered ring in the presence of bases and exclusively via ring cleavage in the presence of AgNO3. 2. syn-1-Fluoro-1-bromo-2-arylcyclopropanes do not react in the presence of AgNO3 at 50°C, but are more reactive than the anti isomers in the presence of bases. 3. Electron-donor substituents on the aromatic ring of 1-fluoro-1-bromo-2-arylcyclopropanes accelerate the reaction in the presence of electrophilic agents and inhibit the reaction on addition of a base. 4. Logarithms of the relative rate constants for the reaction of 1-fluoro-1-bromo-2-arylcyclopropanes with methanol in the presence of AgNO3 correlate with Brown's σ* constants. 5. The reaction of 1-fluoro-1-bromo-2-arylcyclopropanes with alcohol in the presence of bases occurs via sequential elimination and addition.