Abstract
AbstractThe one‐bond nucleophilic reactivities of seven cyclic α‐diazo carbonyl compounds in dichloromethane were determined by analyzing the kinetics of their reactions with benzhydrylium ions (one‐bond reference electrophiles) at 20 °C according to the Mayr‐Patz equation. Though not calibrated for pericyclic reactions, the identified nucleophilicities also reflect relative reactivities of the α‐diazo carbonyl compounds in 1,3‐dipolar cycloadditions with dimethyl acetylenedicarboxylate. These (3+2)‐cycloadditions primarily gave spirocyclic 3H‐pyrazoles, which underwent thermal [1,5]‐sigmatropic (van Alphen‐Hüttel) rearrangements to furnish 1H‐pyrazole‐fused tricyclic products.
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