127525-90-0Relevant articles and documents
New Approach for the Synthesis of Isoxazoline-N-oxides
Kunetsky, Roman A.,Dilman, Alexander D.,Ioffe, Sema L.,Struchkova, Marina I.,Strelenko, Yury A.,Tartakovsky, Vladimir A.
, p. 4907 - 4909 (2003)
(Equation Presented) A strategy for the synthesis of isoxazoline-N-oxides (cyclic five-membered nitronates) from primary nitro compounds and olefins is described. The key step of the process involves 1,3-dipolar cycloaddition of corresponding 1-bromosilyl
Redox-regulated divergence in photocatalytic addition of α-nitro alkyl radicals to styrenes
Tsuchiya, Yuto,Onai, Ryota,Uraguchi, Daisuke,Ooi, Takashi
, p. 11014 - 11017 (2020)
A divergent photocatalytic system for the reaction of α-bromo nitroalkanes with styrene derivatives is established, wherein the generation of the persistent nitroxyl radical as a junctional intermediate and suitable tuning of the redox ability of the system constitute the crucial elements for achieving rigorous control over the possible reaction pathways.
Five-membered cyclic nitronates in C-C coupling with 1-(tert;- Butyldimethylsilyloxy)-1-methoxyethylene
Smirnov, Vladimir O.,Sidorenkov, Alexander S.,Khomutova, Yulia A.,Ioffe, Sema L.,Tartakovsky, Vladimir A.
body text, p. 3066 - 3074 (2009/12/01)
Five-membered cyclic nitronates 3 undergo TBSOTf-catalysed C-C coupling reactions with silyl ketene acetal 4 to give good to excellent yields of 3,3-disubstituted N-(OTBS)isoxazolidines 5, which could not be obtained by previously known procedures. The pr
Thermodynamic stability and reactivity of silylated bis(oxy)iminium ions
Khomutova, Yulia A.,Smirnov, Vladimir O.,Mayr, Herbert,Ioffe, Sema L.
, p. 9134 - 9140 (2008/03/17)
(Chemical Equation Presented) Silylation of various nitronates with trialkylsilyl triflates was investigated by applying NMR techniques. In several cases, a flexible nitronate-bis(oxy)iminium ion (as an ion pair with triflate as counterion) equlibrium was found, and its thermodynamic parameters were determined. Elevation of temperature or dilution shifts this equilibrium toward the reactants. Activation parameters for the C,C-coupling reaction of silylated bis(oxy)iminium ions with a series of reference nucleophiles were determined. Estimated electrophilicity of bis(oxy)iminium ions allows one to count on C,C-coupling when partner nucleophilicity is N > 4.
General method for the synthesis of isoxazoline N-oxides from aliphatic nitro compounds
Kunetsky, Roman A.,Dilman, Alexander D.,Struchkova, Marina I.,Belyakov, Pavel A.,Tartakovsky, Vladimir A.,Ioffe, Sema L.
, p. 2265 - 2270 (2008/02/02)
A method for the synthesis of isoxazolines N-oxides from primary aliphatic nitro compounds and olefins based on the 1,3-dipolar cycloaddition of intermediate 1-halo-substituted silyl nitronates, followed by halosilane elimination has been described. The n