Isopropyl halides, pyrolysis

This study on the kinetic chlorine isotope effect in ethyl chloride50 was extended to secondary and tertiary alkyl halides pyrolyses51. The isotope effects on isopropyl chloride and terf-butyl chloride pyrolysis were found to be primary and exhibited a definite dependence on temperature. They increased with increasing methyl substitution on the central carbon atom. The pyrolysis results and model calculations implied that all alkyl chlorides involve the same type of activated complex. The C—Cl bond is not completely broken in the activated complex, yet the chlorine participation involves a combination of bending and stretching modes. 

Pyrolysis of the acetate of benzyl-o-chlorophenylcarbinol at 300° gives the unsaturated halide, o>chlorostilbene. This carbinol is resistant to direct dehydration by potassium hydrogen sulfate at 180°. This method is also superior for the preparation of the olefinic aldehyde, a-isopropyl-acrolein (50%), and the olefinic ketone, methyl isopropenyl ketone (98%). ... 

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