A STUDY OF THE HALOGENATION OF ALIPHATIC HYDROCARBONS AND DERIVATIVES THEREOF.
SHEFFIELD UNIV (ENGLAND) DEPT OF CHEMISTRY
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The halogenation of the n-butyl halides in the gas phase was investigated. To date the fluorination of n-butyl fluoride and the chlorination of n butyl fluoride, chloride and bromide were investigated. It is hoped to extend these investigations to include a study of the bromination of these compounds under similar conditions. The results obtained so far indicate that the effect of the halogen already present in the organic molecule is to retard substitution at the beta-carbon atom, the effectiveness of the halogens being the order F Cl Br there is some evidence that fluorine may deactivate the gamma-position slightly. At present it has only been possible to obtain precise data about substitution at the alpha-carbon atom in chlorination, which is slightly retarded at this position, the effectiveness of the substituent halogens in deactivation being Br Cl approx. F. The selectivity of the attacking atoms is Cl F but they appear to be affected to a different extent by the substituent halogen. Thus fluorination, while remaining far less selective than chlorination, appears to be more affected by the substituent halogen. Some preliminary studies on the effect of other substituents than the halogens were made. Author
- Organic Chemistry