Organomercury/aluminum-mediated acylative cleavage of cyclic ethers

✍ Scribed by Frederick A. Luzzio; Rhiana A. Bobb

• Book ID: 104209120
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 426 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01226-5

✦ Synopsis

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 ~alkoxychloremercurials and acid chlorides. Using mainly tetrahydrofuran and cyclohexene oxide as substrates, the yield of isolated chloroesters ranged from 52 to 96%.