CHROMYL CHLORIDE OXIDATIONS .2. OXIDATION OF STYRENES

Chromyl chloride oxidation of 1-phenylpropene, 2-phenylpropene, and 1,1-diphenylethene gives 1-phenyl-2-propanone, 2-phenylpropanal, and 1,1-diphenylethanal, respectively, as the sole products of rearrangement. The yield of carbonyl product appears to be greatest when one side of the double bond is 1,1-disubstituted. The suggested mechanism involves an electrophilic attack of chromyl chloride at the carbon of the CC double bond to give a resonance stabilized carbonium ion-like intermediate which rearranges to the observed products. © 1969.