Chromic Acid Oxidation of Indans and Tetralins to 1-Inadanones and 1-Tetralones Using Jones and Other Cr(VI) Reagents

Article abstract of DOI:10.1021/jo00214a007

The Jones chromic acid oxidation, ordinarily used for converting secondary alcohols to ketones, has been successfully extended to the oxidation of indans and tetralins to 1-indanones and 1-tetralones, respectively.A sixfold excess of the reagent was commonly used to ensure complete oxidation of starting material.Addition of anhydrous magnesium sulfate or oven-dried silica gel provided a yield increase of 15-20percent. 2,2'-Bipyridinium chlorochromate was also used and found to be effective in all cases, but this reagent requires a longer reaction time and a 16-fold excess.A comparison between these two reagents and CrO3 in acetic acid was made.The Jones reagent being least selective, gives the highest yield of sterically hindered monoketone from 1,2,3,4,5,6,7,8-octahydrophenanthrene.