Issue 2, 1996

Stereochemical control–-nitrones from oximes by 1,3-azaprotio cyclotransfer or 1,2-prototropy

Abstract

Oximes 1a,b and 10 are configurationally stable at elevated temperatures, the (E)-oximes react exclusively via a concerted 1,3-azaprotio cyclotransfer reaction to give 6- and 7-membered cyclic dipoles, respectively, whilst their Z-isomers react via a 1,2-prototropy-cycloaddition sequence furnishing fused isoxazolidines.

Article information

Article type
Paper

Chem. Commun., 1996, 167-168

Stereochemical control–-nitrones from oximes by 1,3-azaprotio cyclotransfer or 1,2-prototropy

C. O'Mahony and F. Heaney, Chem. Commun., 1996, 167 DOI: 10.1039/CC9960000167

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