The cine-rearrangement and cine-substitution of a series of 3-allkyl-2,2-dichlorocyclobutanones have been studied in the context of a synthesis of polyfunctitonalized cyclobutanones which were required as synthetic intermediates. Our studies showed that the scope of the rearrangement is limited to substrates bearing bulky substituents at C-3. In other cases, mixtures of isomeric cyclobutanones are obtained. Reaction of 3-butyl-2,2-dichlorocyclobutanone with methanol in the presence of a base yielded a product of double cine-substitution.
Cagnon, J., Marchand-Brynaert, J., & Ghosez, L. (1996). Study of the cine-rearrangement and the cinesubstitution of 2,2-dihalocyclobutanones. Journal of the Brazilian chemical society on-line, 7(5), 371-377. https://hdl.handle.net/2078.5/44418 (Original work published 1996)