Reduction of dialkoxydihydrofurans, dialkoxytetrahydrofurans, dialkoxydihydropyrans, and dialkoxytetrahydropyrans with LiAlH4 AlCl3 complex

Autor: Kruglikova, R. I., Kralinina, L. N.
Zdroj: Chemistry of Heterocyclic Compounds; June 1972, Vol. 8 Issue: 6 p672-675, 4p
Abstrakt: The reduction of 2,5-dimethoxytetrahydrofurans, 2,5-dimethoxydihydrofurans, 2,6-dialkoxytetrahydropyrans, and 2,6-dialkoxydihydropyrans with mixtures of LiAlH4 and AlCl3 with various component ratios (3:1, 1:1, and 1:3) proceeds with ring opening and the formation of aliphatic ?-alkoxy alcohols. Hydrogenolysis of 2,5-dimethoxy-2,5-dihydrofuran and 2,6-dialkoxy-?3-dihydropyrans is accompanied by a partial reduction of the double bond and the formation of unsaturated alkoxy alcohols and their saturated analogs. A possible mechanism for the hydrogenolysis is discussed.
Databáze: Supplemental Index