Abstract
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 ω-alkoxy alcohols. Hydrogenolysis of 2,5-dimethoxy-2,5-dihydrofuran and 2,6-dialkoxy-Δ3-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.
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Translated from Khimiya, Geterotsiklicheskikh Soedinenii, No. 6, pp. 743–747, June, 1972.
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Kruglikova, R.I., Kralinina, L.N. Reduction of dialkoxydihydrofurans, dialkoxytetrahydrofurans, dialkoxydihydropyrans, and dialkoxytetrahydropyrans with LiAlH4 AlCl3 complex. Chem Heterocycl Compd 8, 672–675 (1972). https://doi.org/10.1007/BF00487455
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DOI: https://doi.org/10.1007/BF00487455