Thermal Behavior of Spiroozonides from Formaldehyde-O-oxide and Tropone Derivatives: A Coarctate Reaction

Spiroozonides of tropones undergo an unusually facile fragmentation via the coarctate Mobius transition state 1. The ozonides are generated from formaldehyde O-oxide and tropone derivatives at −90°C. Depending on the substitution, they fragment at temperatures between −60 to +50°C to give carbon dioxide, formaldehyde, and benzene derivatives.