Reductive Acetoxylation on .alpha.,.alpha.'-dibromocycloalkanones by Ultrasonically Dispersed Mercury

Authors

Albert J. Fry, Wesleyan University
William Donaldson, Marquette UniversityFollow
Geoffrey S. Ginsburg, Wesleyan University

Document Type

Article

Language

eng

Publication Date

1979

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

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.

Comments

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.

Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/858