The acetalization of glyoxal by vicinal diols

✍ Scribed by Farid Hamedi Sangsari; Francine Chastrette; Maurice Chastrette; Alain Blanc; Georges Mattioda

• Book ID: 104589128
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 538 KB
• Volume: 109
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19901090103

✦ Synopsis

Abstract

The structure and stereochemistry of products obtained when vicinal diols are allowed to react with glyoxal were established with the aid of ^13^C 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.