Tetrahedron p. 3329 - 3336 (1983)
Update date:2022-08-05
Topics:
Lechevallier, A.
Huet, F.
Conia, J.M.
Organic peracid oxidation of α-cyclopropylidene ketones and acetals substituted in the vinylic position leads to the corresponding oxaspiropentyl ketones and acetals.Esters are also formed from the products of the Baeyer-Villiger oxidation; they are easily removed from the crude product.Unsubstituted oxaspiropentyl ketones are not obtained by this method; they are obtained by oxidation of oxaspiropentyl alcohols ( formed by epoxidation of α-cyclopropylidene alcohols).The isomerisation, either spontaneous or through reaction with lithium halides, of oxaspiropentyl ketones and acetals, gives 2-acyl-cyclobutanones and corresponding mono-acetals.These new unstable 1,3-diones must be stored in CCl4 solution.They are present in the dione form only.They add water and methanol, in acidic and even in neutral medium, leading to ring opening products. 2-Benzoyl cyclobutanone 4g is easily rearranged into 3,4-dihydro-6-phenyl 2-pyrone 12.Deacetalization of the 2-acyl-cyclobutanones mono-acetals 7B-11b into the corresponding diones is not possible even by the moist silicagel technique.
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Doi:10.1016/S0040-4020(01)88633-6
(1983)Doi:10.1016/j.bmcl.2009.09.117
(2009)Doi:10.1002/ardp.19743070902
(1974)Doi:10.1021/jo00185a039
(1984)Doi:10.1021/jo01032a046
(1964)Doi:10.1007/s10870-010-9719-5
(2010)