Michel Couturier, J. L. Tucker, C. Proulx
May 29, 2002
Citations
0
Influential Citations
13
Citations
Journal
The Journal of organic chemistry
Abstract
5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.