83191-35-9Relevant academic research and scientific papers
Interplay of Conformational and Chemical Transformations of Ortho-Substituted Aromatic Nitroso Oxides: Experimental and Theoretical Study
Chainikova, Ekaterina M.,Yusupova, Alfia R.,Khursan, Sergey L.,Teregulova, Aigul N.,Lobov, Alexander N.,Abdullin, Marat F.,Enikeeva, Leniza V.,Gubaydullin, Irek M.,Safiullin, Rustam L.
, p. 7750 - 7763 (2017)
The mechanism of the photooxidation of aromatic azides containing a substituent at one of the ortho positions (2,4-dimethoxyphenyl azide (1a) and 2-methyl-4-[(2E)-1-methylbut-2-en-1-yl]phenyl azide (1b)) was studied in acetonitrile. The electronic spectra and the kinetic regularities of the consumption of corresponding nitroso oxides, which are the reaction intermediates, were investigated by flash photolysis. Owing to the one-and-a-half order of the C-N and N-O bonds and asymmetric molecule structure these nitroso oxides exist as four conformers (cis/syn, cis/anti, trans/syn, and trans/anti). The conformers differ in the spectral properties and in the reactivity in various irreversible transformations. The only product, (2Z,4E)-4-methoxy-6-oxohepta-2,4-dienenitrile oxide (7a), was observed during photooxidation of 1a, whereas transformations of the nitroso oxide isomers derived from 1b led to a set of stable products: the cis/anti isomer was transformed into (3,4,7-trimethyl-3a,4-dihydro-2,1-benzisoxazol-5(3H)-ylidene)ethanal (10), the trans isomers recombined forming the corresponding nitro and nitroso compounds, and the most reactive cis/syn isomer was transformed into ortho-nitrosobenzyl alcohol 11. The last was oxidized slowly to the corresponding benzaldehyde 12. Interaction of 11 and 12 led to the formation of (Z)-1,2-bis(2-formyl-4-((2E)-1-methylbut-2-en-1-yl)phenyl)diazene-1-oxide (13). The DFT simulation and kinetic modeling of the nitroso oxide transformations as well as the product analysis allowed revealing the fine details of the mechanism of decay for these species.
Synthesis of 6-methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)- and 6-methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)anilines
Gataullin,Ishberdina,Sotnikov,Abdrakhmanov
, p. 438 - 440 (2008/02/01)
Alkenylation of 6-methyl-2-(2-cyclohexen-1-yl)- and 2-(1-cyclohexen-1-yl)anilines with piperylene in the presence of AlCl 3 and transformation of the resulting cyclohexenylanilines into carbazole structures were studied.
Alkenylation of anilines with dicyclopentadiene, cyclopentadiene, and piperylene
Gataullin,Kazhanova,Sagitdinov,Galyautdinov,Fatykhov,Spirikhin,Abdrakhmanov
, p. 280 - 285 (2007/10/03)
Alkenylation of anilines with dicyclopentadiene, cyclopentadiene, and piperylene in the presence of mineral acids and Lewis acids was studied.
ACID-CATALYZED RERRANGEMENT OF N-(1-METHYL-2-BUTENYL)ANILINE
Abdrakhmanov, I.B.,Sharafutdidov, V.M.,Tolstikov, G.A.
, p. 562 - 564 (2007/10/02)
The effect of the nature of the solvents and catalysts on the rerrangement of N-(1-methyl-2-butenyl)aniline was studied..The reaction is catalyzed by the hydrochlorides of aromatic amines and by Lewis acids.The nature of the solvents has an insignificant effect on the course of the rearrangement.
AMINO-CLAISEN REARRANGEMENT AS A METHOD FOR THE SYNTHESIS OF C-SUBSTITUTED ANILINES
Abdrakhmanov, I. B.,Sharafutdinov, V. M.,Nigmatullin, N. G.,Sagitdinov, I. A.,Tolstikov, G. A.
, p. 1278 - 1283 (2007/10/02)
Various C-alkenylanilines were synthesized by an amino-Claisen rearrangement.The composition of the rearrangement products is affected by the nature of the substituents in the benzene ring and at the nitrogen atom of the initial anilines.
