Abstract
Absolute rate studies were carried out on a series of C(SINGLE BOND)H insertion reactions of dimethyldioxirane (1a). The substrates were chosen so that the distance between a single tertiary C(SINGLE BOND)H bond and an OH group could be varied. The measured rate constants indicate that a rate acceleration occurs when the distance between the reacting C(SINGLE BOND)H bond and the OH group permits intramolecular H-bonding stabilization of the transition state. A similar study in related compounds without the OH group showed no effect of chain length on the rate of the C(SINGLE BOND)H insertion reaction. A related study of the epoxidation reaction of la also found an increased rate when chain length permitted intramolecular H-bonding by an OH group.
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