50899-27-9Relevant academic research and scientific papers
Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones
Chen, Fei,Zhu, Fei-Fei,Zhang, Man,Liu, Rui-Hua,Yu, Wei,Han, Bing
supporting information, p. 3255 - 3258 (2017/06/23)
A novel and facile approach to vicinal oxycyanation and aminocyanation of internal unactivated alkenes is developed. This method utilizes the dichotomous reactivity of iminoxyl radical derived from the initiation of β,γ- and γ,δ-unsaturated ketoximes to provide the general difunctionalization of internal alkenes using tert-butyl hydroperoxide (TBHP) as the environmentally friendly oxidant, CuCN as the commercially available cyanating reagent, and pentamethyldiethylenetriamine (PMDETA) as the ligand. By using this protocol, a series of useful cyano-featured isoxazolines and cyclic nitrones were efficiently prepared.
Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles
Kesornpun, Chatchai,Aree, Thammarat,Mahidol, Chulabhorn,Ruchirawat, Somsak,Kittakoop, Prasat
, p. 3997 - 4001 (2016/03/19)
Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.
Thermal Decomposition of Silver Salts of Aryldinitromethanes in the Presence of Unsaturated Systems. Possible Formation of Arylnitrocarbenes
Coutouli-Argyropoulou, E.,Alexandrou, N.E.
, p. 4158 - 4162 (2007/10/02)
Decomposition of several silver salts of aryldinitromethanes at 100 deg C in the presence of 1,1-diarylethylenes leads to the formation of Δ2-isoxazoline N-oxides in moderate yields and to Δ2-isoxazolines as byproducts. The spectral data of the new compou
