REACTION OF ALKYL IODIDES WITH PERACETIC ACID IN PRESENCE OF AROMATIC COMPOUNDS

Treatment of n-alkyl iodides with peracetic acid in the presence of aromatic compounds in acetic acid at 30° affords alkyl acetates and often iodo aromatic compounds in good yields. The rate of the reaction for a mixture of methyl iodide, peracetic acid, and m-xylene can be expressed as v — k[CH3I] [CH3CO3H] and is independent of the concentration of m-xylene. The structure of alkyl iodides affects the yield of iodoaromatic compound in the decreasing order n-alkyl > sec-alkyl > t-alkyl. The reaction mechanism is briefly discussed in terms of the effect of structure on the kinetics and product composition. © 1969, American Chemical Society. All rights reserved.