Aniline Adducts Research Articles

Iron-Catalyzed Intermolecular C-H Amination Assisted by an Isolated Iron-Imido Radical Intermediate.

Here we report the use of a base metal complex [(tBu pyrpyrr2 )Fe(OEt2 )] (1-OEt2 ) (tBu pyrpyrr2 2- =3,5-tBu2 -bis(pyrrolyl)pyridine) as a catalyst for intermolecular amination of Csp3 -H bonds of 9,10-dihydroanthracene (2 a) using 2,4,6-trimethyl phenyl azide (3 a) as the nitrene source. The reaction is complete within one hour at 80 °C using as low as 2 mol % 1-OEt2 with control in selectivity for single C-H amination versus double C-H amination. Catalytic C-H amination reactions can be extended to other substrates such as cyclohexadiene and xanthene derivatives and can tolerate a variety of aryl azides having methyl groups in both ortho positions. Under stoichiometric conditions the imido radical species [(tBu pyrpyrr2 )Fe{=N(2,6-Me2 -4-tBu-C6 H2 )] (1-imido) can be isolated in 56 % yield, and spectroscopic, magnetometric, and computational studies confirmed it to be an S = 1 FeIV complex. Complex 1-imido reacts with 2 a to produce the ferrous aniline adduct [(tBu pyrpyrr2 )Fe{NH(2,6-Me2 -4-tBu-C6 H2 )(C14 H11 )}] (1-aniline) in 45 % yield. Lastly, it was found that complexes 1-imido and 1-aniline are both competent intermediates in catalytic intermolecular C-H amination.

Iron‐Catalyzed Intermolecular C−H Amination Assisted by an Isolated Iron‐Imido Radical Intermediate

AbstractHere we report the use of a base metal complex [(tBupyrpyrr2)Fe(OEt2)] (1‐OEt2) (tBupyrpyrr22−=3,5‐tBu2‐bis(pyrrolyl)pyridine) as a catalyst for intermolecular amination of Csp3−H bonds of 9,10‐dihydroanthracene (2 a) using 2,4,6‐trimethyl phenyl azide (3 a) as the nitrene source. The reaction is complete within one hour at 80 °C using as low as 2 mol % 1‐OEt2 with control in selectivity for single C−H amination versus double C−H amination. Catalytic C−H amination reactions can be extended to other substrates such as cyclohexadiene and xanthene derivatives and can tolerate a variety of aryl azides having methyl groups in both ortho positions. Under stoichiometric conditions the imido radical species [(tBupyrpyrr2)Fe{=N(2,6‐Me2‐4‐tBu‐C6H2)] (1‐imido) can be isolated in 56 % yield, and spectroscopic, magnetometric, and computational studies confirmed it to be an S = 1 FeIV complex. Complex 1‐imido reacts with 2 a to produce the ferrous aniline adduct [(tBupyrpyrr2)Fe{NH(2,6‐Me2‐4‐tBu‐C6H2)(C14H11)}] (1‐aniline) in 45 % yield. Lastly, it was found that complexes 1‐imido and 1‐aniline are both competent intermediates in catalytic intermolecular C−H amination.

A Review On The Metal Complex Of Nickel (Ii) Salicylhydroxamic Acid And Its Aniline Adduct

A Review On The Metal Complex Of Nickel (Ii) Salicylhydroxamic Acid And Its Aniline Adduct

Role of Nickel (II) Salicylhydroxamic Acid and its Aniline Adduct as an Antimicrobial Substitute

The development of drug resistance as well as the appearance of undesirable side effects of certain antibiotics has led to the search of new antimicrobial agents with the goal to discover new chemical structures which overcome the above disadvantages. As a ligand with potential oxygen and nitrogen donors, hydroxamic acids are interesting and have gained special attention not only because of the structural chemistry of their coordination modes, but also because of their importance in medical chemistry. This study was undertaken to synthesis salicylhydroxamic acid, complex it with nickel (II) and its aniline adduct and evaluate the antimicrobial potential of the ligand and its complex in order to orient future investigations towards the finding of new potent and safe antimicrobial drugs. Solubility, conductivity, UV spectroscopy and antimicrobial studies of the compounds was carried out Salicylic hydroxamic acid (SHA) and Nickel (II) complex showed significant in vitro antibacterial and antifungal activities against all tested organisms. The mode of action by which SHA exhibited antifungal and antibacterial activities may involve the formation of a hydrogen bond through the nitrogen and oxygen atoms in Salicylic hydroxamic acid (SHA) with the active centers of the cell constituents, resulting in interference with the normal cell process. There is great potential for the development of Ni (SHA)2 C6 H5 NH2 into a potent drug with better efficacy than the current antimicrobial therapies available which are easily prone to resistance.

Copper-Mediated Cross-Dehydrogenative Coupling of 2-Methylpyridine and 8-Methylquinoline with Methyl Ketones and Benzamides.

A synthetic method to prepare (E)-(pyridin-2-yl)enones and (E)-(quinolin-8-yl)enones that relies on the respective copper(I)-catalyzed formal cross-dehydrogenative coupling (CDC) reaction of 2-methylpyridine and 8-methylquinoline with methyl ketones has been discovered. The mechanism was delineated to follow a pathway involving oxidation of the N-heterocycle to its corresponding aldehyde adduct prior to reaction with the methyl ketone. The versatility and substrate dependent divergence in the reactivity of the copper-mediated CDC strategy was exemplified by its application to the synthesis of N-(quinolin-8-ylmethyl)amide and N-(quinolin-8-ylmethyl)aniline adducts on switching the cross-coupling partner to benzamides or an aniline derivative.

Electrochemical oxidation and protein adduct formation of aniline: a liquid chromatography/mass spectrometry study

Historically, skin sensitization tests are typically based on in vivo animal tests. However, for substances used in cosmetic products, these tests have to be replaced according to the European Commission regulation no. 1223/2009. Modification of skin proteins by electrophilic chemicals is a key process associated with the induction of skin sensitization. The present study investigates the capabilities of a purely instrumental setup to determine the potential of commonly used non-electrophilic chemicals to cause skin sensitization by the generation of electrophilic species from the parent compound. In this work, the electrophiles were generated by the electrochemical oxidation of aniline, a basic industrial chemical which may also be released from azo dyes in cosmetics. The compound is a known sensitizer and was oxidized in an electrochemical thin-layer cell which was coupled online to electrospray ionization-mass spectrometry. The electrochemical oxidation was performed on a boron-doped diamond working electrode, which is able to generate hydroxyl radicals in aqueous solutions at high potentials. Without any pretreatment, the oxidation products were identified by electrospray ionization/time-of-flight mass spectrometry (ESI-ToF-MS) using their exact masses. A mass voltammogram was generated by plotting the obtained mass spectra against the applied potential. Oligomerization states with up to six monomeric units in different redox states of aniline were observed using this setup. This approach was extended to generate adducts between the oxidation products of aniline and the tripeptide glutathione. Two adducts were identified with this trapping experiment. Protein modification was carried out subsequently: Aniline was oxidized at a constant potential and was allowed to react with β-lactoglobulin A (β-LGA) or human serum albumin (HSA), respectively. The generated adducts were analyzed by liquid chromatography coupled to ESI-ToF-MS. For both β-LGA and HSA, aniline adducts were successfully generated and identified.

Electron beam processed plasticized epoxy coatings for surface protection

Epoxy acrylate oligomer (EA) was plasticized by adding different plasticizers such as epoxidized soybean oil, glycerol and castor oil and cured by electron beam (EB). Different irradiation doses (1, 2.5 and 5 Mrad pass −1) were used in the curing process. The effect of both different irradiation doses and plasticizers on the end use performance properties of epoxy acrylate coating namely, pencil hardness, bending test, adhesion test, acid and alkali resistance test were studied. It was observed that incorporation of castor oil in epoxy acrylate diluted by 1,6-hexanediol diacrylate (HD) monomer with a ratio (EA 70%, HD 20%, castor oil 10%) under 1 Mrad pass −1 irradiation dose improved the physical, chemical and mechanical properties of cured films than the other plasticizer. Sunflower free fatty acid was epoxidized in situ under well established conditions. The epoxidized sunflower free fatty acids (ESFA) were subjected to react with aniline in sealed ampoules under inert atmosphere at 140 °C. The produced adducts were added at different concentrations to epoxy acrylate coatings under certain EB irradiation dose and then evaluated as corrosion inhibitors for carbon steel surfaces in terms of weight loss measurements and corrosion resistance tests. It was found that, addition of 0.4 g of aniline adduct to 100 g epoxy acrylate formula may give the best corrosion protection for carbon steel and compete the commercial corrosion inhibitor efficiency with the same concentration.

Synthesis of an Amine−Oleate Derivative Using an Ionic Liquid Catalyst

A facile (and environmentally friendly) reaction between epoxidized methyl oleate and aniline to produce an oleate-aniline adduct, without the formation of fatty amide, was discovered. This reaction was carried out neat, with a catalytic amount of an ionic liquid. No solvent was used, no byproducts were produced, and the ionic liquid could be recovered and recycled. The reaction products were fully characterized by NMR and GC-MS.

Oligoaniline intermediates in the aniline-peroxydisulfate system

Chemical oxidative polymerization of aniline using peroxydisulfate oxidant in aqueous pH 2.5–10.0 buffers yields electrically insulating brown powders that are believed to be mixtures of Michael-type adducts of benzoquinone monoimine and aniline at various stages of hydrolysis. A spectroscopically similar product is formed when solid 1,4-benzoquinone is added to an aqueous solution of aniline at room temperature in the absence of peroxydisulfate. This suggests that the peroxydisulfate oxidant in the aniline/S 2O 8 2− system provides a pathway for the formation of benzoquinone monoimine as an intermediate. Benzoquinone monoimine intermediate could be formed as a result of a Boyland–Sims rearrangement of aniline proceeding via the intermediacy of p-aminophenyl sulfate. Benzoquinone monoimine undergoes a series of conjugate 1,4-Michael-type addition/reoxidation/coupling steps with aniline or p-aminophenyl sulfate yielding the oligoaniline product. The precipitate that is isolated is also in the midst of two simultaneous pH dependent hydrolysis reactions: (i) hydrolysis of the imine groups to quinone, and (ii) hydrolysis of arylsulfates to phenols. The ratio of hydrolysis in each case was determined by the C/N ratio and sulfur elemental analysis values yielding analytical data that is consistent with experimentally determined values and also with our proposed reaction scheme. These findings offer a rationale for the high C/N ratios (>6.0) frequently observed in these systems while tracing the genesis of the residual sulfur in the product to unhydrolyzed arylsulfate. The oligoaniline product has previously been reported to have a novel poly-aza structure consisting of continuously linked –N–N–N– bonds, and alternately also reported to consist of phenazine-type linkages. This study is consistent with the latter and describes a pathway to phenazine coupling through a second and third stage hydrolysis of the arylsulfate and reoxidation with peroxydisulfate. There is no pathway for the formation of linear –N–N–N– linkages in the aniline/benzoquinone adduct and the striking similarity between its spectroscopic properties and the aniline/S 2O 8 2− adduct suggests that it is not a preferred pathway under these experimental conditions.

Structure and torsional flexibility of the linkage between guanine and fluorene residues in the deoxyguanosine?aminofluorene and deoxyguanosine?acetylaminofluorene carcinogenic adducts

Potential energy surfaces for rotations around two central CN bonds in N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (AAF–dG) and its deacetylated derivative (AF–dG) were studied using Amber 95 molecular mechanics. Both of these adducts are known to be strong mutagens and carcinogens. New Amber 95 force field parameters were derived for the linkage connecting guanine and fluorene moieties in AAF–dG and AF–dG. For this purpose, we determined ab initio MP2/cc-pVDZ//B3-LYP/6-31G* and polarized continuum model Hartree–Fock/6-31G* potential energy surfaces of smaller model systems that included the N-methylimidazole–acetylaniline and N-methylimidazole–aniline adducts. The molecular mechanics parameters were adjusted to minimize differences between the gas-phase ab initio and molecular mechanics surfaces of these model systems. The resulting parameters were transferred to AF–dG and AAF–dG. The barrier for the rotation of the fluorene residue in AF–dG was found to be less than 2 kcal/mol. Such a small barrier renders the fluorene moiety freely rotatable at room temperature. In contrast, the fluorene rotation in AAF–dG is hindered by a significantly larger barrier of 10 kcal/mol. This barrier corresponds to conformations in which the fluorene and acetyl groups lie in the same plane, and is largely due to steric repulsion. Similarly, the coplanar arrangement of guanine and the bridging amino or acetyl groups is disfavored by 5–10 kcal/mol, with AAF–dG again being the more rigid of the two molecules. Energy minima for a rotation around a bond between guanine and the bridging nitrogen are found at ±80° in AAF–dG, and at 120° and −90° for AF–dG. Overall, the fluorene–dG linkages in AF–dG and AAF–dG adducts have significantly different equilibrium structures and torsional flexibilities. These differences may be contributing factors for the observed disparity in mutagenic effects of these adducts.

Synthesis of the glycidyl aniline adduct and its crosslinking

AbstractSynthesis of the adduct of aniline and glycidyl methacrylate and its polymerization and copolymerization with two diisocyanates are presented. Hexyl diisocyanate representing aliphatic compounds and toluene diisocyanate as the aromatic compound were used. UV and thermal initiations were applied. The curing process was controlled by FTIR analysis. Thermomechanical properties of the compositions cured at different temperatures were compared. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 95: 524–528, 2005

Evolution of structure and properties of a liquid crystalline epoxy during curing

The evolution of structure, and thermal and dynamic mechanical properties of a liquid crystalline epoxy during curing has been studied with differential scanning calorimetry (DSC), polarized optical microscopy, x-ray scattering, and dynamic mechanical analysis. The liquid crystalline epoxy was the diglycidyl ether of 4,4′-dihydroxy-α-methylstilbene (DGEDHMS). Two curing agents were used in this study: a di-functional amine, the aniline adduct of DGEDHMS, and a tetra-functional sulfonamido amine, sulfanilamide. The effects of curing agent, cure time, and cure temperature have been investigated. Isothermal curing of the liquid crystalline epoxy with the di-functional amine and the tetra-functional sulfonamido amine causes an increase in the mesophase stability of the liquid crystalline epoxy resin. The curing also leads to various liquid crystalline textures, depending on the curing agent and cure temperature. These textures coarsen during the isothermal curing. Moreover, curing with both curing agents results in a layered structure with mesogenic units aligned perpendicular to the layer surfaces. The layer thickness decreases with cure temperature for the systems cured with the tetra-functional curing agent. The glass transition temperature of the cured networks rises with increasing cure temperature due to the increased crosslink density. The shear modulus of the cured networks shows a strong temperature dependence. However, it does not change appreciably with cure temperature. © 1997 John Wiley & Sons, Inc. J Polym Sci B: Polym Phys 35: 2363–2378, 1997

Monitoring of Aromatic Amine Exposures in Workers at a Chemical Plant With a Known Bladder Cancer Excess

In April 1991, an excess of bladder cancer cases among workers employed at a chemical manufacturing facility in Niagara Falls, NY, was reported. This excess was primarily confined to 708 workers who had ever been employed in the rubber chemicals manufacturing area of the plant, where the aromatic amines aniline and o-toluidine have historically been used. An environmental and biological monitoring survey was conducted to evaluate current exposures to aniline and o-toluidine in the rubber chemicals department. Personal air sampling for aniline and o-toluidine was conducted with the use of a modified Occupational Safety and Health Administration (OSHA) 73 method. Urine samples were collected before and after work (i.e., pre-shift and post-shift, respectively) and stored at -70 degrees C. Base hydrolysis was used to convert acetanilide and N-acetyl-o-toluidine, metabolites of aniline and o-toluidine present in the urine, to the parent compounds. The parent compounds were extracted from the alkaline urine into butyl chloride and then back-extracted from the butyl chloride into aqueous hydrochloric acid. An aliquot of each acidic extract was subjected to ion-interaction reversed-phase liquid chromatography with coulometric electrochemical detection. Hemoglobin (Hb) was extracted from blood and stored at -70 degrees C. For the measurement of adducts of aniline, o-toluidine, and 4-aminobiphenyl (4-ABP), precipitated Hb was dissolved in 0.1 M sodium hydroxide in the presence of recovery standards, and the hydrolysate was extracted with hexane, derivatized with pentafluoropropionic anhydride, and analyzed by gas chromatography-mass spectrometry with negative chemical ionization. A total of 73 workers, including 46 of 64 exposed workers who were employed in the rubber chemicals department and had the potential for exposure to aniline and o-toluidine and 27 of 52 unexposed workers employed in other departments where aniline and o-toluidine were not used or produced, had data available for both aniline and o-toluidine and Hb adducts; 28 of the workers in the former group also had personal air-sampling data. Personal air sample measurements showed that airborne concentrations of aniline and o-toluidine were well within the limits allowed in the workplace by OSHA. Urinary aniline and o-toluidine levels, however, were substantially higher among exposed workers than among unexposed control subjects. The most striking differential was for post-shift urinary o-toluidine levels, which averaged (+/- standard deviation) 2.8 micrograms/L (+/- 1.4 micrograms/L) in unexposed subjects and 98.7 micrograms/L (+/- 119.4 micrograms/L) in exposed subjects (P = .0001). Average aniline-Hb and o-toluidine-Hb adduct levels were also significantly higher (P = .0001) among exposed workers than among unexposed control subjects. Average levels of adducts to 4-ABP, a potential contaminant of process chemicals, were not significantly different (P = .48), although three exposed workers had 4-ABP levels above the range in unexposed workers. The adduct data suggest that, among current workers, o-toluidine exposure substantially exceeds aniline exposure and that 4-ABP exposure, if it occurs at all, is not widespread. These data support the conclusion that occupational exposure to o-toluidine is the most likely causal agent of the bladder cancer excess observed among workers in the rubber chemicals department of the plant under study, although exposures to aniline and 4-ABP cannot be ruled out.

Biomonitoring of urinary aromatic amines and arylamine hemoglobin adducts in exposed workers and nonexposed control persons.

The renal excretion of arylamines in occupationally exposed and nonexposed subjects was measured by a gas chromatography-electron capture detector method. Additionally, in the occupationally exposed persons hemoglobin adduct levels of arylamines were determined by a liquid chromatography-electrochemical detector method, together with the individual acetylator status. The aromatic amines aniline, p-toluidine, 2-naphthylamine, and 4-chloro-o-toluidine were detected in the urine of nonsmoking subjects who were not occupationally exposed to arylamines. Significantly higher concentrations of aniline, o-toluidine, m-toluidine, 2-naphthylamine, and 4-methyl-1,3-phenylenediamine could be observed in the urine of smoking control persons in comparison to nonsmokers. Comparison of smokers and nonsmokers in a group of workers primarily exposed to aniline and 4-chloroaniline revealed significant differences (P < 0.05) in the formation of 4-aminodiphenyl hemoglobin adducts and in the renal excretion of 2-naphthylamine. The slow acetylators in this group produced significantly more hemoglobin adducts of aniline and 4-chloroaniline than did the fast acetylators. In slow acetylators among the smoking workers there was a significant increase in the formation of 4-aminodiphenyl hemoglobin adducts and in the renal excretion of 4-chloroaniline and m-toluidine. The results indicate that there are influences of smoking habits and acetylator status on the levels of arylamine hemoglobin adducts as well as urinary arylamine concentrations. Hemoglobin adducts seem to be good parameters for monitoring aniline and 4-chloroaniline exposure at the workplace, especially if the acetylator polymorphism can be taken into account. 4-Aminodiphenyl hemoglobin adducts might be good parameters for monitoring individual smoking habits. The determination of urinary arylamine concentrations provides additional information concerning acute exposures to aromatic amines.

Preparation and structural studies of tungsten(VI)diolato adducts of phenol and aniline

The tungsten(VI)diolato complex, [W(eg)(pin) 2] (H 2eg = 1,2-ethanediol, H 2pin = 2,3-dimethyl-2,3-butanediol) forms adducts with phenol and aniline. X-ray structural studies and spectral measurements (UV and IR) show that the formation of those adducts is due to hydrogen bonding between OH or NH 2 groups of adductant and diolato oxygen atoms. The effect of hydrogen bonding on the octahedral WO 6 centre is minimal, but the conformation angles of the five-membered chelate ring change considerably. Hydrogen bonding does not promote alcoholato exchange reactions.

Aminolysis of Dicationic Ruthenium Thiophene Complexes

Dicationic sandwich complexes containing thiophene, 2-methylthiophene, 2,5-dimethylthiophene, and tetramethylthiophene react with ammonia to give salts of the formula [(ring)Ru(SC{sub 4}R{sub 4}NH{sub 2})]X where ring = C{sub 6}Me{sub 6} or cymene. The thiophene, 2-methylthiophene, and 2,5-dimethylthiophene complexes undergo C-S cleavage to give iminium-thiolato derivatives. In the case of the 2,5-dimethylthiophene complex, a kinetic isomer was isolated which slowly isomerized to a thermodynamic isomer. The ammonia adducts of the tetramethylthiophene complexes [(cymene)Ru(C{sub 4}Me{sub 4}S)]{sup 2+} and [(C{sub 5}Me{sub 5})Rh(C{sub 4}Me{sub 4}S)]{sup 2+} do not undergo C-S cleavage. These 2-NH{sub 2}C{sub 4}Me{sub 4}S complexes react with protic acids to regenerate the starting dication [(ring)M(C{sub 4}Me{sub 4}S)]{sup 2+}. The aniline adducts of thiophene, 2-methylthiophene, and 2,5-dimethylthiophene are similar to the ammonia derivatives. The structures of the kinetic isomer of [(C{sub 6}Me{sub 6})Ru(SC{sub 3}H{sub 2}MeCHNHPh)]PF{sub 6} and the thermodynamic isomer of [(cymene)Ru(SC{sub 3}H{sub 2}MeCMeNHPh)]OTf were established by single-crystal X-ray diffraction. The crystallographic study proves that the isomerization in this family of compounds arises from the relative configuration at the terminal carbon of the alkenyl thiolate ligand Bond distance data indicate an interaction between the iminium carbon center and the Ru atom in the kinetic isomer. 20 refs., 2 figs., 5 tabs.

Large Transition State Imbalance in the Expulsion of Arylnitromethane Anions from Aniline Adducts of .alpha.-Nitrostilbenes

Aniline adducts of α-nitrostilbenes, PhCH(HNC 6 H 4 Z)CH(C 6 H 4 Y)NO 2 ha- ve been synthesized for a variety of Z/Y combinations. In several cases a mixture of two diastereomers was obtained. Structural assignment of the diastereomers was based both on 1 H NMR and reactivity data. The kinetics of the breakdown of the adducts into the respective benzalani- lines and arylnitromethane anions was studied in acidic 50% Me 2 SO-50% water solutions at 5 o C. The rate constants, k exp , were found to be independent of buffer concentration and pH, indicating a unimolecular mechanism. There is a strong dependence on the aniline substituent (ρ = -2.2) and the pK a of the arylnitromethanes (β 1g =-1.28).

Phase transformations of a liquid crystalline epoxy during curing

The phase transformations of a novel liquid crystalline epoxy, diglycidyl ether of 4,4′-dihydroxy-α-methylstilbene (DGEDHMS), from isotropic phase to liquid crystalline phase during curing have been studied using a cross-polarized optical microscope equipped with a hot-stage. Time-temperature-transformation (TTT) diagrams were constructed following the isothermal curing of the DGEDHMS in the isotropic phase with a difunctional amine, the aniline adduct of the DGEDHMS, and a tetrafunctional sulfonamido amine, sulfanilamide. Our results show that curing with the difunctional amine results in a nematic-like texture, while curing with the tetrafunctional sulfonamido amine leads to a smectic-like texture. Furthermore, curing with the difunctional amine gives rise to a faster development of the liquid crystalline phase, but with a less stable mesophase as compared to the tetrafunctional curing agent. These results are explained in terms of intermolecular interaction and the chain conformation anisotropy resulting from the curing reactions. The TTT diagram will be useful for providing guidelines for processing these new liquid crystalline epoxy systems.

Epoxidized linseed oil‐free fatty acids modified with substituted anilines as antioxidants and antirads for SBR vulcanizates

AbstractEpoxidized linseed oil‐free fatty acids were reacted with aniline and three isomers of toluidine, anisidine, and chloroaniline in such a manner that the carboxylic groups remained free. The prepared adducts were evaluated as antioxidants and antirads for styrene butadiene rubber (SBR) vulcanizates. It was found that 2 phr of orthotoluidine, paraanisidine, orthochloroaniline, and aniline adducts were the best antioxidants and/or antirads. © 1993 John Wiley &amp; Sons, Inc.

Reaction between isoprene and aniline on complex palladium catalysts

Isoprene and aniline have been reacted on the catalytic system Pd(acac)2-Ph3P to form a mixture of isomeric telomers: N-(dimethyloctadien-2,7-yl-1)anilines and N-(dimethyloctadien-1,7-yl-3)anilines but on the catalytic system Pd(acac)2-Ph3P-CF3COOH the main product is a mixture of N-(methylbuten-2-yl)aniline adducts. The reaction between N-methylaniline and isoprene on the latter catalyst also gives a mixture of N-methyl and N-(methylbuten-2-yl)aniline adducts.