We describe the first synthesis of spiroepoxy-beta-lactones obtained via epoxidation of ketene dimers. These compounds display unexpected stability that may be due to a double anomeric effect garnered from analysis of bond lengths by X-ray crystallography of one spirocycle in comparison to calculated bond lengths of related structures. These new strained intermediates display interesting reactivity leading to a butenolide, an alpha-hydroxyketone, a triol, an alpha-chloroketone, and an alpha-azidoketone.
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Duffy et al. (2005) studied this question.
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