1583276-76-9Relevant academic research and scientific papers
Iminoxyl radical-promoted dichotomous cyclizations: Efficient oxyoximation and aminooximation of alkenes
Peng, Xie-Xue,Deng, Yun-Jing,Yang, Xiu-Long,Zhang, Lin,Yu, Wei,Han, Bing
supporting information, p. 4650 - 4653 (2015/01/08)
A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from β,γ- and γ,δ-unsaturated ketoximes, respectively.
Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones
Peng, Xingao,Tong, Benny Meng Kiat,Hirao, Hajime,Chiba, Shunsuke
, p. 1959 - 1962 (2014/03/21)
A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K+ and the oxime oxygen and negatively charged alkene moiety. Basic ring building: A method for the synthesis of cyclic nitrones by using alkenyl oximes was developed based on hydroamination mediated by an inorganic base. DFT calculations for the reaction pathway suggested that this hydroamination could proceed through nucleophilic amination of the unactivated alkene by the oxime nitrogen atom, with the transition state stabilized by ionic interaction with a metal cation such as K+. Copyright
