Download PDF
Synthesis 1987; 1987(9): 806-809
DOI: 10.1055/s-1987-28079
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Lewis Acid-Promoted Favorskii-Type Ring Contraction of Some Cyclic α-Bromo Ketones and Their Acetals

Swaraj B. Maiti* , S. R. Ray Chaudhuri, Amareshwar Chatterjee
  • *Department of Chemistry, Jadavpur University, Calcutta 70032, India
Further Information

Publication History

Publication Date:
12 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The α-bromo cycloalkyl aryl ketones 2a-d on heating with zinc chloride in methanol furnished in moderate to good yields the ring-contracted products 3a-d having gem methyl carbomethoxy function. The acetals of the related α-bromo ketones 7a-c, lacking the methyl group on the halogen-bearing carbon atom, afforded in acceptable yields the ring-contracted esters 8a-c when heated in protic solvent. The limitation of the present ring-contraction procedure has been discussed.

      >