In eliminative ring fission of cyclopropanes by the (E1cB)Rmechanism, gem-dimehtyl substitution substantially raises ΔH‡; for oxirans, which react by the E2 mechanism, this retro-Thorpe–Ingold effect is insufficient to make ring cleavage rate-determining.
P. P. Piras and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 1982, 660 DOI: 10.1039/C39820000660
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