Terent'ev Alexander O, Platonov Maxim M, Krylov Igor B, Chernyshev Vladimir V, Nikishin Gennady I
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.
Org Biomol Chem. 2008 Dec 7;6(23):4435-41. doi: 10.1039/b809661a. Epub 2008 Oct 20.
It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give previously unknown structures of 1-hydroperoxy-1'-alkoxyperoxides in yields up to 64%. The same compounds are formed in the iodine-catalyzed reactions of geminal bishydroperoxides with enol ethers. The nature of the solvent has a decisive influence on the formation of 1-hydroperoxy-1'-alkoxyperoxides. In the series of Et(2)O, THF, EtOH, CHCl(3), CH(3)CN, and hexane, the best results were obtained with the use of Et(2)O or THF as the solvent.
研究发现，偕二氢过氧化物与缩醛的碘催化反应仅发生一个烷氧基被过氧基团取代的情况，从而生成产率高达64%的前所未知结构的1-氢过氧基-1'-烷氧基过氧化物。偕二氢过氧化物与烯醇醚的碘催化反应也生成相同的化合物。溶剂的性质对1-氢过氧基-1'-烷氧基过氧化物的形成具有决定性影响。在乙醚、四氢呋喃、乙醇、三氯甲烷、乙腈和己烷系列中，使用乙醚或四氢呋喃作为溶剂可获得最佳结果。
