Epoxidation of ethylenic linkages by chromic acid IV. Oxidation of triaryl olefins by chromium trioxide
- 1 August 1970
- journal article
- research article
- Published by Wiley in Journal of Chemical Technology & Biotechnology
- Vol. 20 (8) , 256-260
- https://doi.org/10.1002/jctb.5010200806
Abstract
The oxidation of 1,1,2‐triphenylbut‐1‐ene by chromium trioxide in acetic anhydride gives 1,2‐epoxy‐1,1,2‐triphenylbutane with fission products and 1,1,2‐triphenylacetylethylene. Cis‐ and trans‐1‐p‐chlorophenyl‐1,2‐diphenylprop‐1‐ene yield crystalline epoxides in satisfactory yields under similar conditions. The epoxides are stable towards aqueous sulphuric acid. 1,1,2‐Triphenylethylene, 1,1‐di‐(p‐chlorophenyl)‐2‐phenylethylene and 1,1‐di‐(p‐bromophenyl)‐2‐phenylethylene are similarly oxidised but the epoxides are hydrated to the glycols by the action of aqueous sulphuric acid.Chromic acid in aqueous sulphuric acid brings about oxidative fission of the double bond without any rearrangement.Keywords
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