Reductive Acetoxylation on α, α's-Dibromocycloalkanones by Ultrasonically Dispersed Mercury

Journal Article (Journal Article)

The α, α's-dibromocycloalkanones of ring size 5-12 were reduced by ultrasonically dispersed mercury in acetic acid. Products were the corresponding cycloalkanone and α-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. © 1979, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Fry, AJ; Donaldson, WA; Ginsburg, GS

Published Date

  • January 1, 1979

Published In

Volume / Issue

  • 44 / 3

Start / End Page

  • 349 - 352

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo01317a008

Citation Source

  • Scopus