Abstract
The 2,3-dihydrooxepin ring opens upon deprotonation with strong base presumably through an allylic anion which is predicted to be 15 kcal/mol lower in energy than the vinylic anion. Allylic deprotonation occurs with allyl angle expansion whereas vinylic deprotonation results in vinyl angle compression. The vinyl anion of 2,3-dihydrooxepin is stabilized by 8 kcal/mol relative to the vinyl anion of 1,3-cycloheptadiene suggesting that the presence of the oxygen lowers the energy of the vinyl anion.
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