Stereochemistry of dehydration of oxolanes to dienes on γ-alumina
Abstract
On γ-alumina gaseous (±)-2,2,3,4,5,5-hexamethyloxolane (1) is converted mainly into 2,3,4,5-tetramethylhexa-1,5-dine, while its meso-isomer (2) reacts at a higher rate than (1) to give 2,3,4,5-tetramethylhexa-2,4-diene with high selectivity; this is the first reported experimental observation of the stereochemistry of this dehydration reaction.