Abstract
1. A variety of new o-carbomethoxy-ω-diazoacetophenones and isochromane-1,4-diones were synthesized. 2. The decomposition of o-carbomethoxy-ω-diazoacetophenones in methanol-H2SO4, in constrast to reactions of their o-unsubstituted analogs, takes place via the A-SE2 mechanism. The intramolecular nucleophilic assistance of the o-CO2CH3 group increases the decomposition rate of ω-diazoacetophenones by 13–25 times. 3. A correlation was observed between the acid-catalyzed reaction rates of o-carbomethoxy-ω-diazoacetophenones and Hammet's σ constants for benzene ring substituents.
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