59816-86-3Relevant academic research and scientific papers
Synthesis and physicochemical properties of poly[2-(cyclohex-2-en-1-yl)aniline] as a new polyaniline derivative
Andriianova, Anastasia N.,Gribko, Diana E.,Petrov, Ivan S.,Mullagaliev, Ilnur,Sattarova, Alina F.,Salikhov, Renat B.,Abdrakhmanov, Ildus B.,Mustafin, Akhat G.
, p. 6356 - 6366 (2021)
In this study, a new polyaniline (PANI) derivative, poly[2-(cyclohex-2-en-1-yl)aniline], was synthesized for the first time. It was shown by varying the synthetic parameters that the highest polymer yield was obtained if HNO3and (NH4)2S2O8were used. It was found that variation in the conditions for synthesizing poly[2-(cyclohex-2-en-1-yl)aniline] resulted in changes in the optical properties, for example, the PANI derivative obtained in HClO4medium and in the presence of (NH4)2S2O8demonstrated the highest luminescence quantum yield (0.05). Using thermogravimetric analysis of poly[2-(cyclohex-2-en-1-yl)aniline], the main three stages of the polymer thermal degradation were identified. Processing of thermogravimetric curves allowed us to calculate the kinetic and thermodynamic parameters of the thermal degradation of the polymer at various heating rates. The use of poly[2-(cyclohex-2-en-1-yl)aniline] as a sensitive material in resistive sensors showed a high response of electrical conductivity to the changes in humidity (% RH) and ammonia concentration in the environment. The presented results demonstrate an efficient method for PANI modification that favors an improvement in solubility, appearance of photoluminescent properties, and broadening the practical application.
InBr3-Catalyzed Cyclization of Glycals with Aryl Amines
Yadav, Jhillu S.,Reddy, Basi V. S.,Rao, Katta V.,Raj, Kavuda Saritha,Prasad, Atlaluri R.,Kumar, Singarapu Kiran,Kunwar, Ajit C.,Jayaprakash, Panjula,Jagannath, Bulusu
, p. 5198 - 5201 (2003)
A new class of carbohydrate analogues, benzo-fused heterobicycles 1, can be prepared by cyclization of D-glucals with aryl amines in the presence of 10 mol% indium tribromide under mild and convenient reaction conditions [Eq. (1)]. The structure and configuration of the products were established by extensive NMR experiments and molecular modeling studies.
InCl3-catalyzed alkylation of aromatic and heteroaromatic compounds with cyclic allylic acetates
Yadav,Subba Reddy,Vishweshwar Rao,Purushothama Rao,Sarita Raj,Prasad,Prabhakar,Jagadeesh
, p. 3447 - 3450 (2006)
Various aromatic and heteroaromatic compounds undergo smooth alkylation with cyclic allylic acetates in the presence of 10 mol% of indium trichloride under mild conditions to afford 3-substituted indoles, 2-substituted furan and pyrrole and cyclohexenyl-s
On the Superior Activity of In(I) versus In(III) Cations Toward ortho-C-Alkylation of Anilines and Intramolecular Hydroamination of Alkenes
Li, Zhilong,Yang, Shengwen,Thiery, Guillaume,Gandon, Vincent,Bour, Christophe
, p. 12947 - 12959 (2020/11/23)
An efficient ortho-C-alkylation of unprotected anilines with a variety of styrenes and alkenes using a univalent cationic indium(I) catalyst is reported. Mechanistic studies revealed that the reaction likely proceeds via a tandem hydroamination/Hofmann-Martius rearrangement. The high compatibility between the cationic indium(I) complex and primary anilines led us to develop an In(I)+-catalyzed hydroamination of alkenes using unprotected primary and secondary alkenylamines. Computations support the catalytic activity of naked In(I)+ ions, with an outer sphere mechanism for the C-N bond formation and a potentially inner sphere protodemetallation.
Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Bronsted acids
Motokura, Ken,Nakagiri, Nobuaki,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 6006 - 6015 (2008/02/10)
(Chemical Equation Presented) We have developed an environmentally benign synthetic approach to nucleophilic substitution reactions of alcohols that minimizes or eliminates the formation of byproducts, resulting in a highly atom-efficient chemical process. Proton- and metal-exchanged montmorillonites (H- and Mn+-mont) were prepared easily by treating Na +-mont with an aqueous solution of hydrogen chloride or metal salt, respectively. The H-mont possessed outstanding catalytic activity for nucleophilic substitution reactions of a variety of alcohols with anilines, because the unique acidity of the H-mont catalyst effectively prevents the neutralization by the basic anilines. In addition, amides, indoles, 1,3-dicarbonyl compounds, and allylsilane act as nucleophiles for the H-mont-catalyzed substitutions of alcohols, which allowed efficient formation of various C-N and C-C bonds. The solid H-mont was reusable without any appreciable loss in its catalytic activity and selectivity. Especially, an Al3+-mont showed high catalytic activity for the α-benzylation of 1,3-dicarbonyl compounds with primary alcohols due to cooperative catalysis between a protonic acid site and a Lewis acidic Al3+ species in its interlayer spaces.
Design of arylimine postmetallocene catalytic systems for olefin polymerization: I. Synthesis of substituted 2-cycloalkyl- and 2,6-dicycloalkylanilines
Oleinik,Oleinik,Abdrakhmanov,Ivanchev,Tolstikov
, p. 1423 - 1427 (2007/10/03)
A convenient synthetic approach to substituted 2-cycloalkyl- and 2,6-dicycloalkylanilines, involving catalytic hydrogenation on Raney nickel in methanol of readily available o-cycloalkenylanilines prepared by reaction of cyclic alkyl halides with anilines
Intramolecular cyclization of ortho-(cyclohex-2-enyl)anilines. Modified synthesis of ellipticine
Mustafin,Khalilov,Ismagilov,Baimetov,Spirikhin,Abdrakhmanov,Tolstikov
, p. 2121 - 2126 (2007/10/03)
It was found that the reactions of arylamines with 3-bromocyclohexene afforded hydrocarbazole compounds in 64-78% yields. A modified procedure for the synthesis of antitumor alkaloid ellipticine was proposed.
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.
