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Communication | Regular issue | Vol 38, No. 10, 1994, pp.2165-2169
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6848
Novel Ring Expansion Reaction of Epoxides and Oxetanes Accompanied by Rearrangement of Ethereal Functional Groups

Akichika Itoh, Yukihiro Hirose, Hirotaka Kashiwagi, and Yukio Masaki*

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Small cyclic ethers, epoxides and oxetanes, possessing ethereal groups on the side chain, was found to rearrange by means of Lewis acid catalysts, BF3·EtO2, to give ring expanded cyclic ethers accompanied by transfer of the ethereal groups. Formation of tetrahydro-furan and pyran ring and transposition of benzylic and allylic groups of the ethereal function were observed to be favorable.