Chemical and biological oxidation of organohalides. Peracid oxidation of alkyl iodides

TL Macdonald, N Narasimhan…

Index: Macdonald, Timothy L.; Narasimhan, N.; Burka, Leo T. Journal of the American Chemical Society, 1980 , vol. 102, # 26 p. 7760 - 7765

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Citation Number: 33

Abstract

Abstract: The peracid oxidation of seven alkyl iodides has been examined in nonpolar solvents. The stoichiometry for the reaction is shown to be (8+ n) ArC03H+ 6RI+ 3H20-(8+ n) ArC02H+ 6ROH+ 212+ 1205+(n/2) 02 (R= n-heptyl, Ar= m-C1CsH4, n= 4-16). Evidence is presented for the intermediacy of an alkyliodosyl compound in these oxidations. Primary alkyl iodides give exclusively displacement products, whereas secondary iodides give a ...