John E. Bercaw

Selective Hydroxylation of Hydrocarbons by Platinum Salts in Aqueous Media: Direct Conversion of Ethanol to Ethylene Glycol

Water-soluble organic compounds are hydroxylated by aqueous solutions of chloroplatinum(II) and chloroplatinum(IV) salts. p-Toluenesulfonic acid is converted stepwise to the corresponding alcohol and aldehyde, the first step being somewhat faster than the second. No further conversion to the carboxylic acid is observed. Ethanol shows substantial selectivity for attack at a C-H bond of the methyl group, affording ethylene glycol and 2-chloroethanol, as well as more expected products such as acetaldehyde and acetic acid. The origin of the unusual selectivity patterns is discussed in terms of the mechanism of activation of C-H bonds by Pt(II) species.