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

Authors: Hassannia, Ali; Piercy, Graeme; Merbouh, Nabyl

Source: Letters in Organic Chemistry, Volume 6, Number 6, September 2009 , pp. 478-480(3)

Publisher: Bentham Science Publishers

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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.

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

Document Type: Research article

DOI: 10.2174/157017809789124849