Regio- and Stereo-Controlled Alkoxyiodination of 1,3-Diene Using Iodine-Cerium(IV) Ammonium Nitrate
作者:C. Akira Horiuchi、Haruomi Hosokawa、Miyuki Kanamori、Yukiko Muramatsu、Keiko Ochiai、Eiji Takahashi
DOI:10.1246/cl.1995.13
日期:1995.1
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 1,3-diene derivatives using this synthetic method afforded the 1,2-addition alkoxyiodo compounds preferentially.
1,3-环烯烃(环戊二烯、环己二烯和环庚二烯)与碘-铈(IV)硝酸铵在醇中反应,主要生成相应的区域选择性反式-2-烷氧基-1-碘化物,同时伴随有1,4-二烷氧基化合物作为副产品。在使用CH3CN-H2O作为溶剂的情况下,获得了反式-碘醇。因此,使用这种合成方法反应环状和非环状1,3-烯烃衍生物,主要得到1,2-加成烷氧基碘化物。