A new alkoxy-, hydroxy- and nitratoiodination of alpha,beta-unsaturated esters and amides using iodine-ammonium cerium (IV) nitrate and cerium (IV) sulfate

摘要

The reactions of electron-deficient alpha,beta-unsaturated esters using beta-ammonium cerium (IV) nitrate (CAN) or I-2-cerium (IV) sulfate (CS) in alcohols (methanol, ethanol, or 1-propanol) under 50 C-reflux give the corresponding beta-alkoxy-alpha-iodo esters in good yields. In the case of MeCN and MeCN-H2O, beta-nitrato- and beta-hydroxy-alpha-iodo compounds are obtained. The reaction of methyl acrylate (1), ethyl acrylate (2), ethyl crotonate (3), and ethyl methacrylate (4) using I-2-CS give the corresponding beta-hydroxy-alpha-iodo esters in good yields compared with those using I-2-CAN.