Nucleophilicities of Cyclic α-Diazo Carbonyl Compounds

The kinetics of the reactions of cyclic α-diazo carbonyl compounds with electrophilic benzhydrylium ions were evaluated to determine the Mayr reactivity descriptors N (and sN) of the nucleophiles. Interestingly, the thus obtained N scale also reflects relative reactivities of the diazo compounds in 1,3-dipolar cycloadditions with dimethyl acetylenedicarboxylate