Preparation and structure elucidation of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane

✍ Scribed by Bruce Gaede; Rodger Henry; Steven A. Chamberlin

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 179 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370553

✦ Synopsis

Abstract

The tricyclic title compound, a symmetrical dispiro oxygen heterocycle, was isolated as a byproduct in the hydrogenation of furfuryl alcohol in the presence of hydrochloric acid. NMR studies and single crystal X‐ray analysis have established the relative stereochemistry of the two ketal carbons. Formation of the observed trans stereoisomer under equilibrating conditions is attributed to the anomeric effect.