Regio- and Stereo-Controlled Alkoxyiodination of 1,3-Diene Using Iodine-Cerium(IV) Ammonium Nitrate

Article abstract of DOI:10.1246/cl.1995.13

Reaction of 1,3-cycloalkadienes (cyclopentadiene, cyclohexadiene, and cycloheptadiene) with iodine-cerium(IV) ammonium nitrate in alcohols, gave the corresponding regiospecific trans-2-alkoxy-1-iodo compounds as major products accompanied with 1,4-dialkoxy compounds as by-products.In the case of CH3CN-H2O as solvent, trans-iodohydrins were obtained.Thus the reaction of cyclic and acyclic i671,3-diene derivatives using this synthetic method afforded the 1,2-addition alkoxyiodo compounds preferentially.