A STUDY OF THE EFFECT OF SUBSTITUENTS AND OF SOLVENT ON THE REACTIVITY OF THE NORMAL AND ABNORMAL POSITIONS OF UNSYMMETRICAL ORGANIC EPOXIDES
Abstract
The effects of substituents and solvents on the reaction between styrene oxide and benzylamine were investigated. The rate measurements on the reactions of 6 substituted styrene oxides with benzylamine were made in ethanol and methanol. Application of the Hammett equation shows that, as in ethanol, rho is positive for the normal reaction and negative for the abnormal reaction. The effect of substituents in the benzylamine molecule was determined by a kinetic study of the reactions of m-chloro- and 3,4-dimethylbenzylamine with styrene oxide in ethanol at 3 temperatures. The results supported the similarity between the mechanisms for the normal and abnormal reactions. A kinetic study of the reactions of alpha-methyl-, trans-beta-methyl-, and o-methyl-styrene oxide with benzylamine in ethanol showed that the beta-methyl group reduces the rate of attack at both positions very considerably, while the alpha-methyl group reduces the rate of normal attack slightly and that of abnormal attack considerably, and the o-methyl group has surprisingly little effect of the rate of attack at either position. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Jan 01, 1970
- Accession Number
- AD0277947
Entities
People
- R.e. Parker
Organizations
- University of Southampton