Abstract
The thermal decomposition of saturated alkyl chloroformates in the liquid phase results in the formation of rearranged alkyl halides by what is considered to be an ion-pair mechanism. In the presence of pyridinium chloride (0·05 mol.) the decomposition is accelerated and appears to proceed largely by a chain of SN2 displacements; in certain systems (Prn, Bun, Bui, n-pentyl, 3-methylbutyl) the formation of rearranged products and olefins is thus completely eliminated. Isomerically pure 1-chloro-2,2-dimethylpropane is obtained by the decomposition of the 2,2-dimethylpropyl chloroformate–pyridine complex. Olefinic products from chloroformate pyrolyses may be accounted for in part by a carbonium-ion mechanism although the formation of alk-1-enes as the principal olefins from s-alkyl chloroformates is probably due to the operation of an intramolecular cis-elimination.
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