Reductive Acetoxylation on .alpha.,.alpha.'-dibromocycloalkanones by Ultrasonically Dispersed Mercury
American Chemical Society
The Journal of Organic Chemistry
The α,α'-dibromocycloalkanones of ring size 5-12 were reduced by ultrasonically dispersed mercury in acetic acid. Products were the corresponding cycloalkanone and -acetoxycycloalkanone. The ratio of these two is quite sensitive to ring size, and this fact is used to support the intermediate formation of 2-hydroxyallyl cations as precursors of the keto acetates. Molecular mechanics calculations support the proposed mechanism.
Fry, Albert J.; Donaldson, William; and Ginsburg, Geoffrey S., "Reductive Acetoxylation on .alpha.,.alpha.'-dibromocycloalkanones by Ultrasonically Dispersed Mercury" (1979). Chemistry Faculty Research and Publications. 858.
The Journal of Organic Chemistry, Vol. 44, No. 3 (1979): 349-352. DOI.
William A. Donaldson was affiliated with Hall-Atwater Laboratories of Chemistry, Wesleyan University at the time of publication.