Synthesis of a functionalized furan via ozonolysis—further confirmation of the Criegee mechanism

A new method for the synthesis of a tetrahydrofuran ring is described which involves ozonolysis of a diene possessing a free hydroxy group in the γ-position. The reaction proceeds via ozone attack on the terminal double bond, cleavage, and intramolecular cyclization through the free hydroxy group. The cyclization event can be rationalized through formation of Criegee’s carbonyl oxide, but not through the ‘unified’ mechanism, thereby lending support to the Criegee mechanism as a method of producing oxygen-containing heterocycles.