SYNTHESIS OF 4-ALKYL-2-IODOSOBENZOIC ACIDS - POTENT CATALYSTS FOR THE HYDROLYSIS OF PHOSPHORUS ESTERS

The syntheses of five new 4-alkyl-2-iodosobenzoic acids (3) are described. The iodine atom was introduced by ortho-directed lithiation of 4-alkylbenzyl alcohols followed by treatment with I2. The catalytic effectiveness of each of the products in the hydrolysis of 4-nitrophenyl diphenyl phosphate in microemulsions was studied. The 4-methyl- and 4-ethyl-substituted products were each found to be significantly better catalysts than the standard nonalkylated 2-iodosobenzoic acid (3, R = H). These results would indicate that microemulsions of these materials may find use in detoxification procedures. © 1990, American Chemical Society. All rights reserved.