15568-73-7Relevant articles and documents
5,5-Dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups
Couturier, Michel,Tucker, John L.,Proulx, Caroline,Boucher, Ghislain,Dube, Pascal,Andresen, Brian M.,Ghosh, Arun
, p. 4833 - 4838 (2007/10/03)
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 α-functionalization.