109787-18-0Relevant academic research and scientific papers
Reaction of N-(phenyl and methyl)-C-arylnitrones with DMAD in ionic liquid: Efficient synthesis of Δ4-isoxazolines
Valizadeh, Hassan,Vesally, Esmail,Dinparast, Leila
experimental part, p. 106 - 110 (2012/05/05)
Facile synthesis of N-(methyl and phenyl)-Δ4-isoxazolines via the reaction of (Z)-N-(methyl and phenyl)- C-arylnitrones with dimethyl acethylenedicarboxylate, DMAD, in ionic liquid is described. (Z)-Nmethyl- C-arylnitrones afforded the high yie
Rapid, highly efficient, and room-temperature TiCl4-catalyzed synthesis of 4-Isoxazolines under Solvent-Free Conditions
Valizadeh, Hassan,Dinparast, Leila
experimental part, p. 291 - 297 (2011/03/20)
Δ4-Isoxazoline derivatives were synthesized in excellent yields via the titanium tetrachloride-catalyzed 1,3-dipolar cycloaddition reaction of nitrones withαβ,-unsaturated compounds under neat conditions at room temperatures in very short react
Thiones as superdipolarophiles. Rates and equilibria of nitrone cycloadditions to thioketones
Huisgen, Rolf,Fisera, Lubor,Giera, Henry,Sustmann, Reiner
, p. 9671 - 9678 (2007/10/02)
1,3-Dipolar cycloadditions of N-methyl-C,C-diphenylnitrone (15) and N-methyl-C-phenylnitrone (16) with aliphatic thioketones are equilibrium reactions. The 1,4,2-oxathiazolidines were characterized and their dissociation constants measured by 1
Silyl Group Transfer in the Cycloaddiition Reactions of Silyl Iminium Salts Derived from Aryl-Substituted Oximes
Padwa, Albert,Dent, William H.,Schoffstall, Allen M.,Yeske, Philip E.
, p. 4430 - 4437 (2007/10/02)
Reaction of the iminium salt derived from benzaldehyde oxime and (trimethylsilyl)methyl triflate with cesium fluoride gives rise to azomethine ylides.Dipolar cycloaddition proceeded with complete stereospecificity with dimethyl fumarate and maleate.In sha
Benzaldehyde Oxime as a 1,3-Dipole Chameleon
Padwa, Albert,Dent, William,Yeske, Philip E.
, p. 3944 - 3946 (2007/10/02)
Reaction of the iminium salt derived from benzaldehyde oxime and (trimethylsilyl)methyl triflate with cesium fluoride in the presence of electron-dificient alkenes gives rise to azomethine ylide cycloadducts.In sharp contrast, reaction of the salt with alkynes produces dipolar cycloadducts derived from nitrones.
SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES
Cristina, D.,Amici, M. De,Micheli, C. De,Gandolfi, R.
, p. 1349 - 1357 (2007/10/02)
The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.
