Synthesis, Structure, and Reactivity of Unexpectedly Stable Spiroepoxy-β-Lactones Obtained by Epoxidation of 4-Alkylidene-2-Oxetanones
- 12 November 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (48) , 16754-16755
- https://doi.org/10.1021/ja053478h
Abstract
We describe the first synthesis of spiroepoxy-β-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 α-hydroxyketone, a triol, an α-chloroketone, and an α-azidoketone.Keywords
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