97206-73-0Relevant academic research and scientific papers
Ruthenium-catalyzed intermolecular coupling reactions of arylamines with ethylene and 1,3-dienes: Mechanistic insight on hydroamination vs ortho-C-H bond activation
Yi, Chae S.,Sang, Young Yun
, p. 2181 - 2183 (2005)
(Chemical Equation Presented) The cationic ruthenium complex [(PCy 3)2(CO)(Cl)Ru=CHCH=C(CH3)2] +BF4- was found to be an effective catalyst for the coupling reaction of aniline and ethylene to form a ～1:1 ratio of N-ethylaniline and 2-methylquinoline products. The analogous reaction with 1,3-dienes resulted in the preferential formation of Markovnikov addition products. The normal isotope effect of kNH/kND = 2.2 (aniline and aniline-d7 at 80°C) and the Hammett ρ = -0.43 (correlation of para-substituted p-X-C6H4NH2) suggest an N-H bond activation rate-limiting step for the catalytic reaction.
Addition of Phenylnitrenium Ion to Olefins. Reactions of Phenyl Azide with Some Olefins in the Presence of Trifluoroacetic Acid
Takeuchi, Hiroshi,Koyama, Kikuhiko,Mitani, Michiharu,Ihara, Rie,Uno, Tomoko,et al.
, p. 677 - 684 (2007/10/02)
Addition to cyclohexene, cis- or trans-4-methylpent-2-ene, or hex-1-ene of a singlet phenylnitrenium ion, generated from phenyl azide in the presence of trifluoroacetic acid, gave stereo- or regiospecifically N-phenyl-β-hydroxylamines (after work-up with aqueous Na2CO3) via aziridinium ions together with N-allyl and 2- and/or 4-allylanilines.Use of methyl acrylate or methyl crotonate as an electron-deficient olefin led to the formationof N-phenylserine or N-phenylthreonine methyl ester (after work-up with with aqueous Na2CO3), respectively.In the reaction with 1,1-disubstituted ethylene or styrene derivatives, N-substituted anilines were formed through an attack of either tertiary alkyl or benzylic cations on phenyl azide.
Stereospecific Addition of Singlet Phenylnitrenium Ion to Some Alkenes. Reactions of Phenyl Azide with Alkenes in the Presence of Trifluoroacetic Acid
Takeuchi, Hiroshi,Ihara, Rie
, p. 175 - 177 (2007/10/02)
Stereospecific addition to some alkenes of a singlet phenylnitrenium ion, generated from phenyl azide in the presence of trifluoroacetic acid, gives aziridinium ions; this addition is followed by ring-opening reactions of aziridinium ions.
