Unsaturated carbohydrates. Part 21. A carbocyclic ring closure of a hex-5-enopyranoside derivative

Abstract

Heating of the unsaturated glycoside triester (1) in refluxing aqueous acetone with mercury(II) chloride gave the cyclohexenone derivative (4) in high yield in a reaction which represents a new means of obtaining functionalised carbocyclic compounds from carbohydrates. From compound (4), the substituted cyclohexenone (5) and thence the phenol (6) were prepared.