Karolina Kula

Cracow University of Technology | PK · Department of Organic Chemistry and Technology

Pyrazolines are five-membered heterocyclic compounds with two nitrogen atoms in their structure. They have many applications, especially in medicines. The following work presents the experimental and theoretical studies on the reaction between 3,3,3-trichloro-1-nitroprop-1-ene (TNP) 1 and N-(4-bromophenyl)-C-arylnitrylimine (NIs) 2a-c. The experim...

The possibility of the construction of five-membered heterocycles, including single heteroatom or systems with two, three and four heteroatoms were critically reviewed based on the recent reports regarding to the [3+2] cycloaddition reactions. Almost all of analysed reaction are realized with high regio- and stereoselectivity.

The nitrovinyl moiety is surely one of the most reactive fragments in organic chemistry, continuously employed to explore original pathways and reach new targets. One of the most important classes of chemicals containing this fragment are nitro-functionalised analogues of 1,3-butadiene. In this paper a comprehensive review study of these compounds...

This paper assesses various approaches that use captured greenhouse gases (GHG) as feedstocks for chemical synthesis. The analysis focuses mainly on the two most abundant anthropogenic GHG, such as carbon dioxide (CO 2 ) and methane (CH 4 ), as well, their conversion technologies to obtain methanol (MeOH), formic acid (FA) and dimethyl carbonate (D...

Quinone methides are a class of biologically active compounds that can be used in medicine as antibacterial, antifungal, antiviral, antioxidant, and anti-inflammatory agents. In addition, quinone methides have the potential to be used as pesticides, dyes, and additives for rubber and plastics. In this paper, we discuss a subclass of quinone methide...

By exploiting the unique reactivity of ethynyl-phosphonites we obtain novel P(V)-containing five-membered heterocycles via (3+2)-cyclization reactions with aldehydes or cycloaliphatic thioketones in satisfactory to excellent yields. Whereas reactions with thioketones to yield 1,3-thiaphospholes-3-oxides occur smoothly at room temperature with equim...

The regioselectivity of the [3+2] cycloaddition reactions between trans-β-nitrostyrene and C,N-diarylnitryle imine analogues as three atom components (TACs) has been studied with the use of Conceptual Density Functional Theory in the framework of Molecular Electron density Theory. Global and local reactivity indices were determined. Presented quant...

The experimental and theoretical studies of reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromopnenyl)-C-arylnitrylimine was performed. It was found, that the title process lead unexpectedly to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of expected 2-pyrazoline molecular system. This is a result of unique CHCl3 elemination...

Pyrrolidines are important heterocyclic organic compounds which show biological effects. Many of them are successfully used in medicine. These compounds can also be applied in industry, for example as dyes or agrochemical substances. Therefore, the study of pyrrolidines chemistry is important for modern science. In this paper the pyrrolidines synth...

This poster summarises author's research of reaction between N-methylazomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene. Both synthetic and computational approach were discussed.

The poster shows results of study of [3+2] cycloaddition reaction between (Z)-C-(9-anthryl)-N-methylnitrone and analogues of trans-β-nitrostyrene. In the research computational approach based on MEDT was applied.

The question of the reactivity of different substituted nitrylimine-type three atom components (TACs) in [3+2] cycloaddition (32CAs) reactions with electrophilically activated nitroethenes was explored within the Molecular Electron Density Theory (MEDT). In the course of parallel research, the molecular mechanism of considered transformation was ex...

The regioselective zw-type [3 + 2] cycloaddition (32CA) reactions of a series of aryl-substituted nitrile N-oxides (NOs) with trichloronitropropene (TNP) have been both experimentally and theoretically studied within the Molecular Electron Density Theory (MEDT). Zwitterionic NOs behave as moderate nucleophiles while TNP acts as a very strong electr...

The molecular mechanisms of addition of dihalocarbenes and dimethoxycarbene to thioketones derived from 2,2,4,4-tetrmethylcyclobutane-1,3-dione were examined on the basis of the DFT wb97xd/6-311g(d,p)(PCM) calculations. Obtained results demonstrated that the examined processes exhibit polar nature and in the case of electrophilic dichloro-, and dib...

The large and significant increase in carbon dioxide concentration in the Earth's atmosphere is a serious problem for humanity. The amount of CO2 is increasing steadily which causes a harmful greenhouse effect that damages the Earth's climate. Therefore, one of the current trends in modern chemistry and chemical technology are issues related to its...

The present paper is a continuation of comprehensive study regarding to synthesis and properties of pyrazoles and their derivatives. In its framework an experimental and theoretical studies of thermal decomposition of the 3,3-diphenyl-4-(trichloromethyl)-5-nitropyrazoline were performed. It was found, that the decompositions of the mentioned pyrazo...

The regiochemistry of [3+2] cycloaddition (32CA) processes between benzonitrile N-oxide 1 and β-phosphorylated analogues of nitroethenes 2a–c has been studied using the Density Functional Theory (DFT) at the M062X/6-31+G(d) theory level. The obtained results of reactivity indices show that benzonitrile N-oxide 1 can be classified both as a moderate...

The [3+2] cycloaddition (32CA) reactions of cyclic azomethine ylides with a series of acetylene derivatives have been studied within the Molecular Electron Density Theory (MEDT). Analysis of the Conceptual DFT indices allows the characterisation of the ambiphilic character of these cyclic AYs, thus participating as strong electrophiles and strong n...

The regioselectivity of the [3+2] cycloaddition reactions between benzonitrile N-oxide as three-atom component and two series of para-substituted β-nitrostyrene analogues was analysed in the framework of a Molecular Electron Density Theory. All of the considered processes were found to be initiated by the attack of the most nucleophilic oxygen atom...

The participation of different diaryldiazomethanes as three-atom components (TACs) in [3+2] cycloaddition reactions with (E)-3,3,3-trichloro-1-nitroprop-1-ene was analysed. All of the examined reactions occur with full regioselectivity, leading to respective 3,3-diaryl-4-trichloromethyl-5-nitro-Δ1-pyrazolines. Contrary to other known nitro-Δ1-pyraz...

(E)-3,3,3-Trichloro-1-nitroprop-1-ene undergoes [3+2] cycloaddition reaction with N-aryl(pyridin-3-yl) nitrones under mild conditions. The reaction is fully regio- and stereoselective and gives expected nitro-substituted nicotine analogs with 3,4-cis-4,5-trans-stereoconfiguration.

The mechanism of the reaction of diphenyldiazomethane with thiobenzophenone and related hetaryl thioketones leading to the corresponding tetrasubstituted thiiranes was studied by means of DFT computational methods at the M06‐2X/6‐311+G(d) level of theory. The study showed that the initial step of this conversion is a classic one‐step (3+2) cycloadd...

Searching for new antibacterial agents is getting more and more challenging due to increasing drug resistance, which has become a major concern in the field of infection management. Our study presents synthesis and characterization by IR, UV, 1H-NMR and 13C-NMR spectra, a homogenous series of β-EWG functionalyzed β-nitrostyrenes, which could be can...

In this review we present recent progress in the cycloaddition reactions of conjugated nitroalkenes with alkenes, conjugated 1,3-dienes or three atoms components (eg. nitrones, azides, diazocompounds, azomethine imines and ylides).

Oxidation of fullerenes, carbon nanotubes, and graphene, is one of the first proposed and successful approaches for further functionalization of these nano dimension carbon allotropes. Also, the C20fullerene, as the smallest known carbon cage, is one of the most important species, in the future of nanotechnology. In this regard, the potential energ...

A molecular mechanism of the [3+2] cycloaddition has been explored using various DFT theoretical levels. It was found that the reaction proceeds via transition states with different synchronicity, but no intervention of the theoretical possible zwitterionic intermediates. Additionally, regioselectivity of the cycloaddition process has been analysed...

Simple, efficient, clean, and stereospecific protocols of protection of phosphorus atom with borane and deprotection from the borane complexes of the tertiary phosphines in mild conditions are reported. The proposed protection/deprotection reactions tolerate a range of functional groups and lead to pure products with excellent yield with no need fo...

In the contrast to all known [3+2] cycloadditions between nitrones and conjugated nitroalkenes, reactions of (E)-3,3,3-trichloro-1-nitroprop-1-ene with (Z)-C-(9-anthryl)-N-arylnitrones are proceeding in a fully regio- and stereoselective manner. Additionally, DFT calculations suggest stepwise, zwitterionic mechanism of these cycloadditions.

Reactions between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene lead to acyclic 2,3-diazabuta-1,3-diene derivatives, instead of the expected pyrazoline systems. DFT calculations suggest that this is a consequence of formation of zwitterionic structure in the first stage of the reaction. It must be noted that this is a specific property of the...

New structure undergoing enhancement Space Group: Pna21, Cell: a 17.1599(18)Å b 15.0993(19)Å c 5.7829(6)Å, α 90° β 90° γ 90°

A series of new N-alkyl substituted N-oxides of C-(9-anthracene)-imines have been synthesized . The structure of the compounds has been confirmed by spectral data.