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

Full Text: HTML

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 ...

Related Articles:

Rhenium complex-catalyzed acylative cleavage of ethers with acyl chlorides

[Umeda, Rui; Nishimura, Takashi; Kaiba, Kenta; Tanaka, Toshimasa; Takahashi, Yuuki; Nishiyama, Yutaka Tetrahedron, 2011 , vol. 67, # 38 p. 7217 - 7221]

Alkoxycarbonylation of aryl iodides using gaseous carbon monoxide and pre-pressurized reaction vessels in conjunction with microwave heating

[Kormos, Chad M.; Leadbeater, Nicholas E. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 1 p. 65 - 68]

Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium

[Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709]

Iron??Catalyzed One??Pot Oxidative Esterification of Aldehydes

[Wu, Xiao-Feng; Darcel, Christophe European Journal of Organic Chemistry, 2009 , # 8 p. 1144 - 1147]

A fast and simple method for the acylation of alcohols with acid chlorides promoted by metallic samarium

[Jia, Xue-Shun; Wang, Hai-Long; Huang, Qing; Kong, Ling-Long; Zhang, Wei-He Journal of Chemical Research, 2006 , # 2 p. 135 - 138]

More Articles...