2,2′-dihalo-bis(perfluorocycloalkenes): Part II. Reaction with pyridine

Pyridine reacts with 2,2′-dichloro(perfluorobicycloalken-l-yl) under hydrolytic conditions to give the pyridinium betaine of a 1,3-diene. Hydrolysis of the allylic fluorines occured exclusively in the cyclobutenyl ring bearing the oxygen anion. The intermediate ylide, if indeed formed at all, was too unstable to isolate and identify.