Study of the cine-rearrangement and the cinesubstitution of 2,2-dihalocyclobutanones

Cagnon, JR;Marchand-Brynaert, Jacqueline;Ghosez, Léon
(1996) VII Brazilian Meeting on Organic Synthesis — Location: RIO JANEIRO(Brazil) (8.September.1996)

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  • Cagnon, JR
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
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.
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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)