Organomercury/aluminum-mediated acylative cleavage of cyclic ethers

Article abstract of DOI:10.1016/S0040-4020(98)01226-5

Epoxides and tetrahydrofurans are cleaved with concomitant acylation to chloroalkyl esters using a reagent system composed of an organomercurial, aluminum metal and an acid chloride. The cleavage is promoted under mild conditions by a range of readily-available cyclic β-alkoxychloromercurials and acid chlorides. Using mainly tetrahydrofuran and cyclohexene oxide as substrates, the yield of isolated chloroesters ranged from 52 to 96%.