SVIBOR - Project code: 1-07-187

MINISTRY OF SCIENCE AND TECHNOLOGY

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Project code: 1-07-187


SYNTHESIS AND CHEMISTRY OF ADAMANTANE DERIVATIVES AND RELATED POLYCYCLIC MOLECULES


Main researcher: MAJERSKI, KATA (27342)


Assistants
Type of research: basic
Duration from: 01/01/91. to 12/31/93.
Papers on project (total): 69
Papers on project quoted in Current Contents: 23
Institution name: Institut "Ruđer Bošković", Zagreb (98)
Department/Institute: Department of Organic Chemistry and Biochemistry
Address: Bijenička 54
City: 10000 - Zagreb, Croatia
Communication
Phone: 385 (01) 425-648
Fax: 385 (01) 425-647
E-mail: MAJERSKI@OLIMP.IRB.HR
Summary: As a part of our continuing research in the area of synthesis and reactivity studies of polycyclic molecules we have prepared a numerous adamantane and protoadamantane derivatives. In order to gain insight into the chemical reactivity of nontetrahedral carbon atoms, 1,2-methanoadamantane, a molecule with twist bent sigma bond, as well as adamantane derivatives of small-ring propellanes were prepared and their reactivity toward electrophiles, nucleophiles and free radicals was studied. A part of our project deals with studies of pi-interactions in polycyclic beta,gama-unsaturated ketones in direct and sensitized photolysis and in various solvents. In addition, series of protoadamantanoid ketones have been prepared and their fragmentation paths in mass spectrometer were investigated. Also, specifically labelled mono- and dideuterated adamantane derivatives have been prepared and long-range deuterium isotope effects on carbon-13 chemical shift were studied. As a part of our research, design and syntheses of new macrocyclic polyethers, that contain a polycyclic cage molecule as a rigid lipophilic component, are also included. In a continuation of biological activity studies, 1-(2-phenyl-2-adamantyl)amines were synthesized and their biological activity was compared with that of phencyclidine.

Keywords: photochemistry, beta,gama-unsaturated ketones, acetone-sensitized irradiation, 4-methylene-2-adamantanone, 4-methylene-2-protoadamantanone, 4-methylene-4-homoadamantan-2-one, saturated and unsaturated protoadamantanoid ketones, cyclopropanation, adamantylamine derivatives, biological activity, 2-aminoadamantylcarbonitriles, 4-aminoprotoadamantylcarbonitriles, adamantyl phencyclidine, polynitropolycyclic cage compounds, deuterium isotope effects, cross-ring field effects, carbon-13 chemical shift, remote hyperconjugation, 2-adamantanone isotopomers, 2-substituted adamantanones, 2-methylene-d2-adamantane derivatives, /3.1.1/propellane, polycyclic unsaturated ketones, 1,2-methanoadamantane, twist bent sigma bond, macrocyclic thioethers, trans-bicyclo/4.1.0/hept-3-ene derivatives, substituted brendene derivatives.

Research goals: -Development of new synthetic methods. -Progress in structure-reactivity relationship studies as a tool for better anticipation of organic reactions. -Synthesis of new adamantane derivatives of biological activity. Due to their rigid and well defined geometry, adamantane and related polycyclic compounds have unique structural properties and play a significant role in organic chemistry, as model compounds of reaction mechanism studies, and problems in stereochemistry and spectroscopic investigations. We believe that our investigations have contributed significantly to the present state of knowledge of both, polycyclic chemistry and strain-ring systems. The results are expected to provide a further insight into the reactivity and nature of the unusual bond between nontetrahedral carbon atoms and to extend our knowledge on the chemistry of carbon in general, which is the basis of organic chemistry. The proposed project is well suited for training graduate students and provides a very good basis for specialization in any field of applied or fundamental organic chemistry and for transfer of scientific informations.

COOPERATION - PROJECTS


  1. Name of project: PN 832 Nontetrahedral Saturated Carbon Atoms
    Name of institution: National Science Foundation
    City: DC 20550 - Washington, USA

  2. Name of project: Deuterium Isotope Effects on Nuclear Shielding in Rigid Polycyclic Molecules
    Name of institution: Internationales Buero KFA
    City: 5170 - Juelich, Germany

  3. Name of project: JF-141 Synthesis and Chemistry of Novel Polycarbocyclic Cage compounds. Cage Compounds as Rigid, Lipophilic Units in the Constructions of Macrocyclic Hosts."
    Name of institution: National Science Foundation
    City: DC 20550 - Washington, USA

COOPERATION - INSTITUTIONS


  1. Name of institution: University of Toledo (Prof. James L. Fry), Toledo, OHIO 43606, USA
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: Toledo, USA

  2. Name of institution: University of North Texas (prof. A.P. Marchand)
    Type of institution: University/Faculty
    Type of cooperation: Joint project
    City: Denton, SAD

  3. Name of institution: Universitaet-Gesamthochschule (Prof. H. Guenther)
    Type of institution: University/Faculty
    Type of cooperation: Joint project
    City: Siegen, Njemačka
Other information about the project.
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