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Group XXIII.

GENERAL ORGANIC CHEMISTRY

 

Head of Group:
Prof. Krzysztof Wojciechowski

e-mail: kris@icho.edu.pl

Home Page: http://ww2.icho.edu.pl/kris/
kwhome.htm

1980 - Ph.D. - Department of Chemistry, Warsaw University of Technology

1993 - Habilitation - Institute of Organic Chemistry – Polish Academy of Sciences

2002 - Full Professor

Post-doc, Indiana University – Purdue University, Indianapolis, USA

Research Fellow, Kyoto University, Japan

Visiting professor, Universite de Pau et des pays de l’Adour, Pau, France

Associate Editor of Polish Journal of Chemistry

Associate Editor of Synthetic Communications

List of papers (http://ww2.icho.edu.pl/kris/Papers.htm)

 

 

 

Prof. Mieczys³aw M¹kosza
Professor Emeritus

 

 e-mail: icho-s@icho.edu.pl

Ph.D., 1963, Department of Chemistry, Warsaw University of Technology

Habilitation, 1967, Department of Chemistry, Warsaw University of Technology

Post-doc, Iowa State University, Ames, USA, 1970-71

Full Professor, 1976

Full Member of the Polish Academy of Sciences, Member of the Academia Europea, 

Member of the Deutsche Akademie der Naturforscher Leopoldina

Director of the Institute of Organic Chemistry PAS 1979 - 2004

Visiting Professor, University of Barcelona, 

Universite Paris Sud, Purdue University, Indianapolis

Honorary Professor St. Petersburg University

Tarrant Distinguished Visiting Professor, Florida State University, Gainesville

Doctor Honoris Causa: Indiana University Purdue University Indianapolis; Russian Academy of Sciences, Moscow; Technical University in Gliwice; Ural Technical University, Ekaterinburg; Rostov State University, Rostov

St. Kostanecki Medal of the Polish Chemical Society, 1979; Jurzykowski Foundation Prize, New York 1987; State Prize First Degree, 1988; Prize of Prime Minister of Poland, 1995; Maria Sk³odowska-Curie & Wilhelm Klemm Honorary lectureship of German and Polish Chemical Societes, 1995; Maria Sk³odowska-Curie & Pierre Curie Honorary lectureship of French and Polish Chemical Societes, 1996; Alexander von Humboldt Research Award, 1996; Œniadecki Medal of the Polish Chemical Society, 1997; Honorary Fellow of Florida Center for Heterocyclic Compounds, 1999; Professorial Grant of Foundation for Polish Science, 1999 – 2002.

 

Staff: 

Prof. Mieczys³aw M¹kosza (Professor Emeritus); Sylwia B³a¿ej, Ph. D.; Dariusz Krajewski, Ph. D.; Urszula Karcz, Ph. D. student; Daniel Sulikowski, Ph. D. student; Anna Wojtasiewicz, Ph. D. student.

 

Research activity:

     The main scientific activity is in the field of reactions of nucleophilic agents with electrophiles. For several years we are developing a new field - intermolecular reactions of g-halocarbanions with aldehydes and ketones, imines, the Michael acceptors and other electrophilic partners. These reactions offer new ways of synthesis of substituted tetrahydrofurans, pyrrolidines, cyclopentanes, etc. 

     Our efforts are directed towards discovery of new processes initiated by the formation of σH-adducts of nucleophilic agents to electrophilic arenes. Although Vicarious Nucleophilic Substitution (VNS) reaction described in our early papers is already a well established general methodology for introduction of carbon, oxygen and nitrogen substituents into electrophilic aromatic rings it continues to be a subject of our studies. We are studying fine mechanistic features of this process, namely factors affecting relations of rates of the addition and the elimination processes and consequently to control the orientation of the substitution. 

     We are particularly interested in developing of new reactions of oxidative nucleophilic substitution of hydrogen as well as cine- and tele-substitution in nitroarenes. 

     There is a substantial activity in studies on application of the VNS reaction in the chemistry of heterocyclic compounds, non benzenoid aromatic systems and electrophilic alkenes. Our studies are also directed towards the utilization of the products obtained by the VNS for the synthesis of natural products and compounds of important practical value. 

     Of particular interest are studies on generation and reactions of ortho-quinone methyleneimines (aza-ortho-xylylenes) mostly generated from 1,3-dihydro-2,1-benzisothiazole 2,2-dioxides (benzosultams) products of intramolecular VNS reaction.

 

Selected scientific publications (2005-2008):

  1. M¹kosza M., Loska R. “Introduction of perfluoroalkyl substituents into heteroarenes via nucleophilic substitution of hydrogen” Z. Naturforsch. B 2008 63 (4): 363-374

  2. M¹kosza M, Bujok R. “Synthesis of benzylidenecyclopropanes from gamma-halopropyl pentachlorophenyl Sulfones using a Julia-Kocienski olefination”
    Synlett 2008 (4): 586-588

  3. Loska R., M¹kosza M. “New synthesis of 2-heteroarylperfluoropropionic acids derivatives by reaction of azine N-oxides with hexafluoropropene” Chem. – Eur. J. 2008,  14 (8), 2577-2589.

  4. Modrzejewska H., Wojciechowski K. “Synthesis and Reactions of 3-Halogeno-3-methylbenzosultams” H. Pol. J. Chem. 2008 82, 585-589

  5. Loska R, Majcher M, M¹kosza M “Synthesis of trifluoromethylated azines via nucleophilic oxidative substitution of hydrogen by trifluoromethyl carbanions” J. Org. Chem. 2007 72 (15): 5574-5580

  6. M. Judka, A. Wojtasiewicz, W. Danikiewicz and M. M¹kosza “Halogens in g-position enhance the acidity of alkyl aryl sulfones and alkane nitriles” Tetrahedron  2007,  63, 8902–8909

  7. Barbasiewicz M., Brud A., M¹kosza M. “Synthesis of substituted tetrahydropyrans via intermolecular reactions of delta-halocarbanions with aldehydes” Synthesis 2007 (8): 1209-1213 

  8. M¹kosza M., Surowiec M., Szczepañska A., Sulikowski D., Maltsev O. “Simple and general synthesis of α-(p-nitroaryl) derivatives of alanine and serine“ Synlett 2007 (3): 470-474 

  9. Loska R., M¹kosza M. “Synthesis of perfluoroalkyl-substituted azines via nucleophilic substitution of hydrogen with perfluoroisopropyl carbanions” J. Org. Chem. 2007 72 (4): 1354-1365 

  10. Barbasiewicz M., M¹kosza M. „Intermolecular Reaction of Chlorohydrine Anions: Acetalization of Carbonyl Compounds under Basic Conditions” Org. Lett. 2006, 8, 3745-3748.

  11. Loska R., M¹kosza M. “A Simple Methods for Introduction of Tetrafluoroethyl Substituents into Nitrogen Heterocycles” Mendeleev Comm. 2006, 161-163.

  12. M¹kosza M., Fedoryñski M. “Co-catalysis in Phase Transfer Catalyzed Reactions (a concept paper)” Arkivoc 2006, Part (IV) 7-17.

  13. Florio S., M¹kosza M., Lorusso P., Troisi L. “Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes with an Oxazoline-Stabilized Carbanion” Arkivoc 2006, Part (VI) 59-66.

  14. Barbasiewicz M., M¹kosza M. „Simple Synthesis of Tetrahydrofurans via Reaction of Enolates of γ-Chloroketones with Aldehydes” Synthesis 2006, 1190.

  15. Szmigielski R., Danikiewicz W., Dolatowska K., Wojciechowski K. “Retro Diels–Alder and other electron ionization-induced fragmentation reactions of 1,2,3,4-tetrahydrobenzopyran-2,3-dicarboxylic acid derivatives” Int. J. Mass Spectrom. 2006, 248, 148–154.

  16. Modrzejewska H., Wojciechowski K. "Reactions of aza-ortho-xylylenes generated from 3-aryl-2,1-benzisothiazoline 2,2-dioxides" Pol. J. Chem. 2006, 80, 1695-1702.

  17. Ostrowski S., £opuszyñska B., Mikus A. “Structure Determination of Some Nitro-5,10,15,20-tetrakis(3-methoxyphenyl)porphyrins Using Simple NMR Techniques" Pol. J. Chem. 2006, 80, 1209-1215.

  18. Wyrêbek P., Mikus A., Ostrowski S. "Synthesis of Some Porphyrinyl Dyads Utilizing TPP-Diene Moiety Architectured Around One of the meso-Phenyl Rings" Jordan J. Chem. 2006, 1, 39-45.

  19. Ostrowski S., Raczko A. M. "Selective double functionalization of meso-tetraphenylporphyrin complexes on the same pyrrole unit by tandem electrophilic/nucleophilic aromatic substitution" Helv. Chim. Acta 2005, 88, 974-978.

  20. M¹kosza M., Judka M. "New synthesis of pyrrolidines via reaction of gamma-halocarbanions with imines" Helv. Chim. Acta 2005, 88, 1676-1681.

  21. Ostrowski S., Mikus A. „Synthesis of Porphyrin — Acetylene and Porphyrin-Diene Building Blocks for New Dyads Preparation” Heterocycles 2005, 65, 2339-2346.

  22. M¹kosza M., Bujok R. "Cocatalysis in phase-transfer catalyzed fluorination of alkyl halides and sulfonates" J. Fluorine Chem. 2005, 126, 209-216.

  23. M¹kosza M., Barbasiewicz M., Krajewski D., "Diastereoselective synthesis of tetrahydrofurans via reaction of g,d-epoxycarbanions with aldehydes" Org. Lett. 2005, 7, 2945-2948.

  24. M¹kosza M., Paszewski M. "Oxidative nucleophilic substitution of hydrogen in nitroarenes. A short review" Pol. J. Chem. 2005, 79, 163-178.

  25. Pianowski Z., Staliñski K. „Application of dialkyltin hydrides containing the chiral 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand in radical cyclizations at the steady state” Pol. J. Chem. 2005, 79, 721-729.

  26. Stêpieñ A., Petrosyan A., Wilk M., Staliñski K. “Free radical addition and cyclization reactions of [2-(4-(S)-isopropyl-2-oxazoline)-5-phenyl]dialkyltin hydrides” Pol. J. Chem. 2005, 79, 1015-1024.

  27. Ostrowski S. "Preparation of 2-nitro-5,10,15,20-tetraphenylporphyrin zinc(II) complex - post scriptum to electrophilic nitration of porphyrins at the beta-pyrrolic position" Pol. J. Chem. 2005, 79, 1169-1172.

  28. Modrzejewska H., Wojciechowski K. "Synthesis and reactions of 3-alkylsulfanyl-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides" Tetrahedron 2005, 61, 8848-8854.

  29. Borkin D., Loska R., M¹kosza M. "Trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane (Ruppert reagent) promoted by triphenyldifluorostannates" Pol. J. Chem. 2005, 79, 1187-1191.

  30. Stêpieñ A., Loska R., Cmoch P., Staliñski K. “Application of the radical cascade of acyclic peptide-based precursors into analogues of type I beta-turn” Synlett 2005, 83-86.

  31. Wojciechowski K., Dolatowska K. "Generation of ortho-quinone methides upon thermal extrusion of sulfur dioxide from benzosultones" Tetrahedron 2005, 61, 8419-8422.