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The acetalization of glyoxal by vicinal diols
Abstract
The structure and stereochemistry of products obtained when vicinal diols are allowed to react with glyoxal were established with the aid of 13C NMR structure relationships. Hemiacetalization yields 1,4-dioxane-2,3-diols regardless of the diol reacted. The course of acetalization depends on the structure of the diol: trans-1,2-cyclohexanediol and analogs yield only 1,4,5,8-tetraoxadecalins as acetals, whereas cis-1,2-cyclohexanediol and 1,2-ethanediol yield mixtures containing mostly 2,2′-bi-1,3-dioxolanes. The isomeric distribution of products depends on the reaction conditions.
