The thermal decomposition of 3-chloro and 3-bromo-3-ethyldiazirine in various solvents has been investigated. A comparison was made between the decomposition in gas phase and in solution. The nature of the solvent does not affect the rate of diazirine decomposition, but does alter the subsequent reactions of the carbene. The results show that the cis olefin is predominant in a non-polar solvent but less so in polar solvent. These results were successfully explained by considering the electrostatic interaction of the CH3δ+ and Clδ− groups.
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Liu et al. (1974) studied this question.