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Coulson, Edward Joseph (1964) Interaction of alkyl phosphites with hydrogen halides. Doctoral thesis, Northern Polytechnic.
The first, second and third dealkylations of a number of alkyl phosphates, including the optically active 2-octyl esters, by hydrogen chloride and hydrogen bromide, were investigated by product analysis.
The first and second dealkylations were found to give rise to unrearranged alkyl halides only, except in the example of the isobutyl system when a small amount of rearrangement was observed. It was concluded that the alkyl halides were formed by suggested mechanisms.
The third dealkylation was found to give rise to unrearranged alkyl halides in the examples of primary straight chain esters, but to give some rearrangement in the examples of secondary straight chain esters where such arrangement was possible. Various mechanisms for the formation of the alkyl halides were suggested. The isobutyl system was again found to be peculiar and some rearrangement was observed.
The rate of dealkylation of di-n-butyl hydrogen phosphite by hydrogen chloride in the absence of solvent was determined.
This work constitutes a contribution to the investigation of factors determining the rearrangement or otherwise of simple alkyl groups with special reference to the formation isomerically and optically pure alkyl halides.
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