ChemInform Abstract: Pyridinium Chlorochromate in Organic Synthesis. A Facile and Selective Oxidative Cleavage of Enol Ethers.

ChemInform Abstract

The cyclic enol ethers (I) are oxidized selectively with pyridinium chlorochromate (II) to give the macrocyclic keto lactones (III). Various semicyclic enol ethers such as (IV), (VI), or (IX) react in the same manner to produce the corresponding lactones. The enol ethers (XI) and (XIII) are oxidatively split to yield the keto esters (XII) and (XIV) respectively. However, when dihydroanisol (XV) undergoes this reaction, it is aromatized to give anisole (XVI). The lactone (XVII) does not react under these conditions.