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Murphy, William Stephen (1963) Alkyl isomerisation during formation of alkyl halides. Doctoral thesis, Northern Polytechnic.
The mechanism of decomposition of a series of alkyl dichloroborinates was investigated by product analysis. n-Butyl dichloroborinate was decomposed in a number of solvents and in the presence of catalytic quantities of Lewis acids. The decomposition of optically active 2-ectyl, 2-pentyl and 1-phenylethyl systems, was studied. It was concluded that the alkyl chloride was probably formed by a combination of suggested mechanisms.
Analogy was made between the chloride and the bromide systems. Although the alkyl dibromoborinates were more unstable, the percentage rearrangement was similar to that, which occurred in the formation of alkyl chlorides.
Decomposition of the four isomeric dibutyl chloroboronates was studied. These compounds generally were more stable than the corresponding dichloroborinates. The alkyl chloride were considered to form by a combination of suggested mechanisms. Rearrangements were likewise detected in this system.
The interaction of some alkyl halides with aluminium halides was studied, to confirm the rearrangements observed in the decomposition of the alkyl dihalogenoborinates and dialkyl chlorobornates. A number of mechanisms are suggested.
The catalysed and uncatalysed dealkylations of tri-n-butyl borate with hydrogen chloride and hydrogen bromide were investigated. Little or no rearrangements were observed.
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