10.1016/0040-4020(82)85161-2
The research investigates the rearrangement of oxirane-ethanols via alkoxyetains to produce oxetanes and oxolanes. The study aims to explore the factors influencing the formation of these cyclic compounds and to understand the mechanism of the rearrangement process. The researchers found that the choice between oxetane and oxolane formation depends on the degree of substitution of the oxirane ring and its configuration, with cyclization predominantly occurring at the more substituted carbon and the cis form favoring the formation of the smaller ring. The reaction proceeds with inversion of configuration at the site of oxygen attack, and the presence of a tin atom in a push-pull mechanism significantly aids the ring-opening process. The study concludes that the transposition method offers a convenient route to functional oxetanes, with high yields and minimal by-products. Key chemicals used in the research include oxirane-ethanols, methoxytributyltin, isophthalic acid, and various solvents such as phenylcyclohexane and ethers.