5, 5-Dimethyl-1, 4, 2-dioxazoles as versatile aprotic hydroxamic acid protecting groups

…, JL Tucker, C Proulx, G Boucher, P Dubé…

Index: Couturier, Michel; Tucker, John L.; Proulx, Caroline; Boucher, Ghislain; Dube, Pascal; Andresen, Brian M.; Ghosh, Arun Journal of Organic Chemistry, 2002 , vol. 67, # 14 p. 4833 - 4838

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Citation Number: 11

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 ...