A Simple and Efficient Synthesis of 1,4- and 1,5-Dioxepan-2-one

Title: A Simple and Efficient Synthesis of 1,4- and 1,5-Dioxepan-2-one

Volume: 6 Issue: 6

Author(s): Ali Hassannia, Graeme Piercy and Nabyl Merbouh

Affiliation:

Keywords: TEMPO, 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, 3-(2-hydroxyethoxy) propan-1-ol, oxidative esterification, lactone

Abstract: A novel synthesis of 1,4- and 1,5-dioxepan-2-one lactones was achieved through the regioselective oxidation of 3-(2-hydroxyethoxy)propan-1-ol. Under basic conditions, when 3-(2-hydroxyethoxy)propan-1-ol was oxidized using oxoammonium salts, a quantitative oxidative esterification was observed, resulting in a regioselective lactone ring closure. This oxidation was tailored to afford 1,4-dioxepan-2-one in very good yield.

Cite this article as:

Hassannia Ali, Piercy Graeme and Merbouh Nabyl, A Simple and Efficient Synthesis of 1,4- and 1,5-Dioxepan-2-one, Letters in Organic Chemistry 2009; 6 (6) . https://dx.doi.org/10.2174/157017809789124849