Mikołaj Sadowski

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

The correlation between coefficients from Dimroth equations and descriptors of global electron density transfer was explored based on the data available in the recent literature. We established that the obtained results should be very usable for the interpretation of the organic reactivity and molecular mechanisms.

Microwave assisted reactions are extremely popular. Analysing articles tackling Microwave assisted syntheses of nitrones, some inconsistencies in used methods can be seen. Shortcoming found in the literature are hereby announced and discussed.

The regio-stereoselectivity and the molecular mechanism of the Au(III)-catalysed [3+2] cycloaddition reaction of (Z)-C,N-diphenylnitrone with nitroethene were explored in the light of the DFT calculations. We found, that the presence of the Au(III) molecular segments, in the reaction environment, dramatically has changed the cycloaddition mechanism...

A computational study of Syn-propanethial S-oxide, as a new TAC for [3+2] cycloaddition reactions, was conducted. The study employed MEDT approach. As alkene components various nitroethenes were applied. Local reactivity descriptors N k (local nucleophilicity) and ω k (local electrophilicity) of S-oxide 1, were determined. Mechanisms of the reactio...

In recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. In particular, the application of these compounds as building blocks to obtain heterocy-cles is a popular object of research. Therefore, in continuation of our research devoted to the topic of conjugated nitrodienes, experimental and quantum-chem...

The molecular mechanism of the reaction between 2-methoxyfuran and ethyl 13 (Z)-3-phenyl-2-nitroprop-2-enoate was investigated on the basis of wb97xd/6-311+G(d,p)(PCM) 14 quantum chemical calculations. It was found that the most probable reaction mechanism is fun- 15 damentally different from what was previously postulated. In particular, six possi...

The regio- stereoselectivity and the molecular mechanisms of the [3+2] cycloaddition reactions between the Syn-propanethial S-oxide and selected conjugated nitroalkenes were explored theoretically in the framework of the Molecular Electron Density Theory. It was found, that the cycloadditions with the participation of the nitroethene as well as its...

The regio- stereoselectivity and the molecular mechanism of the Au(III)-catalysed (3+2)-cycloaddition reaction between (Z)-C,N-diphenylnitrone and nitroethene in the benzene solution were evaluated on the basis of the B3LYP18-D3(BJ)/def2svp (PCM) quantum chemical calculations. It was found, that the presence of the Au(III) molecular segments, in th...

The course of the reactions between ethyl oleate and aromatic nitrile N-oxides was reexamined under the laboratory conditions. The reaction course was explained on the basis of the DFT quantumchemical calculations. It was found that independently of the reaction protocol, in any case the expected 2-isoxazolines are not formed. Instead of this, resp...

Currently, the chemistry of conjugated nitrodienes is becoming more and more popular. These molecules are successfully applied in cycloaddition to synthesize six-membered rings in Diels-Alder reactions. Nitrodienes can be also applied to obtain bis-compounds in [3+2] cy-cloaddition. Moreover, the presence of a nitro group in the structure provides...

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...

Currently, the chemistry of conjugated nitrodienes is becoming more and more popular. These molecules are successfully applied in cycloaddition to synthesize six-membered rings in Diels-Alder reactions. Nitrodienes can be also applied to obtain bis-compounds in [3+2] cycloaddition. Moreover, the presence of a nitro group in the structure provides a...

In this work, new nitrones, derived from nicotinaldehyde and N-aryl-N-hydroxylamines are described, and methods for their synthesis, and purification are presented. Spectral characterisation of said nitrones is also presented.

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.

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...

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.