Journal of Organic Chemistry p. 6129 - 6133 (1992)
Update date:2022-08-05
Topics:
Wathen, Steven P.
Czarnik, Anthony W.
N- and O-benzoylhydroxylamines are, in principle, capable of forming five-membered metal chelates structurally similar to those of α-amino esters.Because α-amino esters are hydrolyzed by many metal ions, the metal-promoted or -catalyzed reactions of N- and O-benzoylhydroxylamines were examined.Two metals that are active with α-amino esters - Ni(II) and Zn(II) - show no reaction with either benzohydroxamic acid or O-benzoylhydroxylamine in aqueous solution.Cu(II) accelerates the rate of benzoic acid formation with both compounds by factors of up to 60- and 40-fold, respectively, under the conditions evaluated.Both reactions give benzoic acid as product, but hydroxylamine is not a product in either reaction.We observe that O-benzoylhydroxylamine reacts with Cu(II) with net oxidation and with Cu(I) with net reduction of the nitrogenous product.When a substoichiometric amount of Cu(II) is used, copper serves as a catalyst to effect deacylation with redox disproportionation of the starting material.
View MoreChangzhou Medi-tech Bioscientific Co., Ltd.
Contact:86-519-83246372
Address:Number 115 Menghedadao Road, Changzhou, Jiangsu, China
Huaihua Baohua Biotechnology Co.,Ltd
website:http://www.baochengchem.com
Contact:86-519-82698291
Address:HouYang chemical development zone,Jintan,Jiangsu,China (213200)
Xinchang Jiu Xin Pharmaceutical Co., Ltd
website:http://www.jiuxinpharm.com
Contact:86 137 5756 8585
Address:Poyang industry Park
Shanghai doly chemical Co.,Ltd
Contact:+86-21-34716221
Address:No.328,WuHe Roard,MinHang,ShangHai China
Lyrin Industrial Corporation Limited
Contact:86-731-82571800
Address:Rm 2408,Asia Economy International Building,Shaoshan Road South,Yuhua District,Changsha,Hunan,China
Doi:10.1039/a707812i
(1998)Doi:10.1080/00304940609356000
(2006)Doi:10.1016/j.bioorg.2020.103666
(2020)Doi:10.1021/ja00477a043
(1978)Doi:10.1021/jo01066a602
(1961)Doi:10.1021/ic0351085
(2004)