Synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-beta-lactones obtained by epoxidation of 4-alkylidene-2-oxetanones.
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.
Duffy
Richard J
RJ
Department of Chemistry, Texas A&M University, College Station, 77842-3012, USA.
Morris
Kay A
KA
Romo
Daniel
D