SVIBOR - Papers quoted in CC - project code: 1-07-187
MINISTRY OF SCIENCE AND TECHNOLOGY
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E-mail: ured@znanost.hr
SVIBOR - Collecting Data on Projects in Croatia
Papers quoted in Current Contents on project 1-07-187
Quoted papers: 23
Other papers: 46
Total: 69
Title: Reactive molecules - carbenes
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Hiršl-Starčević, Sanja (44633)
Journal: Kemija u industriji
Number: 1
ISSN: 0022-9830
Volume: 40
Year: 1991
Pages: from 5 to 12
Number of references: 57
Language: hrvatski
Summary: The paper reviews the knowledge of carbene chemistry
(generation of carbenes, typical reactions and mechanisms) with a detailed
presentation of carbene reactivity and selectivity investigations. The
preparation of some strained polycyclic compounds via carbenes is
discussed.
Keywords: carbene reactions, cycloadditions and insertions, preparation of polycyclic molecules by carbene route
Title: 2,4-Dimethylmethano-2,4-didehydroadamantane and its
Reactivity in Relation to the Unsubstituted Analogue
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Šafar-Cvitaš, Dunja (46253)
- Majerski, Zdenko (27353)
Journal: Tetrahedron Letters
Number: 13
ISSN: 0040-4039
Volume: 32
Year: 1991
Pages: from 1655 to 1658
Number of references: 14
Language: engleski
Summary: 2,4-Dimethylmethano-2,4-didehydroadamantane (1) has been
prepared and the gem-dimethyl substituent effects of propellane 1 in
relation to its unsubstituted analogue 2 were studied. The reactivity of 1
is considerably greater than that of 2 due to the higher nucleophilicity of
its central bond. However, 1 is thermally more stable than 2.
Keywords: 2,4-Dimethylmethano-2,4-didehydroadamantane, synthesis and reactivity of, thermal stability of propellane
Title: Evidence for Remote Hyperconjugation through the Long
Range Deuterium Isotope Effects on Carbon-13 Chemical Shifts
- Authors:
- Vinković, Vladimir (71214)
- Mlinarić-Majerski, Kata (27342)
- Marinić, Željko (115246)
Journal: Tetrahedron Letters
Number: 48
ISSN: 0040-4039
Volume: 33
Year: 1992
Pages: from 7441 to 7444
Number of references: 11
Language: engleski
Summary: Linear correlation between deuterium isotope effects(DIE)
through four bonds and chemical shifts of carbon atom in position 2 in 2a-j
demonstrate evidence for remote hyperconjugation. This is consistent with
the Cieplak hyperconjugation model of diastereofacial selection.
Keywords: long-range deuterium isotope effects, remote hyperconjugation, C-13 nmr spectra
Title: Mass Spectral Studies of some Protoadamantanoid Ketones
- Authors:
- Škare, Danko (94313)
- Mlinarić-Majerski, Kata (27342)
- Švob, Vladimir
- Milivojevič, Dušan
Journal: Rapid Communications in Mass Spectrometry
Number: 9
ISSN: 0951-4198
Volume: 6
Year: 1992
Pages: from 571 to 572
Number of references: 14
Language: engleski
Summary: The mass spectra of saturated and unsaturated
protoadamantanoid ketones were studied. Remarkable and unusual loss of
water in 10-protoadamantanone is explained by the flexibility of the
ethano-bridge and the ability for interaction with carbonyl.Three
fragmentation paths of protoadamantanoid ketones are discussed.
Keywords: unsaturated protoadamantanoid ketones, MS spectra of, fragmentations paths
Title: Preparation of Novel 2-Aminoadamantyl- and
4-Aminoprotoadamantylcarbonitriles
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Kaselj, Mira (139620)
- Škare, Danko (94313)
Journal: Organic Preparations and Procedures International
Number: 5
ISSN: 0030-4948
Volume: 24
Year: 1992
Pages: from 501 to 507
Number of references: 10
Language: engleski
Summary: 2-Aminoadamantyl- and 4-protoadamantylcarbonitriles were
prepared in good yields using two different pathways. Mechanism of their
formation is proposed and discussed.
Keywords: aminoadamantylcarbonitriles, synthesis of, mechanism of formation
Title: Long-range Deuterium Isotope Effects in C-13 nmr Spectra
of Adamantane and 2-Adamantanone
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Vinković, Vladimir (71214)
- Meić, Zlatko (30321)
- Gassman, P.G.
- Chyall, L.J.
Journal: Journal of Molecular Structure
Number: 1
ISSN: 0022-2860
Volume: 267
Year: 1992
Pages: from 389 to 394
Number of references: 9
Language: engleski
Summary: Long range deuterium isotope effects through five bonds in
the C-13 spectra of adamantane and 2-adamantanone were found. This is the
first example of effects through five bonds observed in a rigid saturated
systems.
Keywords: long-range deuterium isotope effects, adamantane and 2-adamantanone isotopomers, effects through five bonds
Title: Chiroptical, Structural and Catalytic Properties of
S-alfa-Methyl-(1-substituted
phenyl)-2-(2'-pyrido)-1-ethylidene)benzylamines and their Rh(I) and Cu(I)
Complexes
- Authors:
- Šunjić, Vitomir (104266)
- Šepac, Dragan (170102)
- Kojić-Prodić, Biserka (21602)
- Kiralj, Rudolf
- Mlinarić-Majerski, Kata (27342)
- Vinković, Vladimir (71214)
Journal: Tetrahedron Asymmetry
Number: 3
ISSN: 0957-4166
Volume: 4
Year: 1993
Pages: from 575 to 590
Number of references: 37
Language: engleski
Summary:
S-alfa-Methyl-(1-(substituted-phenyl)-2-(2'-pyrido)-1-ethylidene)benzylamin
es and their Rh(I) complexes were prepared and their chiroptical and
conformational properties were studied. Also their Cu(I) complexes were
prepared "in situ" and catalytic activity in cyclopropanation of styrene
was tested.
Keywords: chiral 1,5-bidentate nitrogen ligands, CD spectra, X-ray crystaland molecular structure, conformation and imine-enamine equilibrium
Title: Definitive Carbon-13 Chemical Shift Assignments in
2-Substituted Adamantane Derivatives by Deuterium Isotope Effects
- Authors:
- Vinković, Vladimir (71214)
- Marinić, Željko (115246)
Journal: Spectroscopy Letters
Number: 7
ISSN: 0038-7010
Volume: 26
Year: 1993
Pages: from 1223 to 1230
Number of references: 14
Language: engleski
Summary: Deuterium isotope effects on carbon-13 chemical shifts in
5-(2H)-isotopomers of ten 2-substituted adamantane derivatives were
determined and used for complete assignment of their carbon-13 NMR spectra.
Keywords: Carbon-13 chemical shifts, deuterium isotope effects, 2-substituted adamantanes
Title: Synthesis and biological activity of phencyclidine and its
adamantylamine derivatives
- Authors:
- Ferle-Vidović, Ana (11656)
- Kaštelan, Marija
- Petrović, Danilo (36926)
- Šuman, Lidija
- Kaselj, Mira (139620)
- Škare, Danko (94313)
- Mlinarić-Majerski, Kata (27342)
Journal: European Journal of Medicinal Chemistry
Number: 3
ISSN: 0223-5234
Volume: 28
Year: 1993
Pages: from 243 to 250
Number of references: 25
Language: engleski
Summary: 1-(2-Phenyl-2-adamantyl)amines 2a-c were synthesized and
their biological activity evaluated by in vitro testing of their effects on
the proliferative and reproductive ability of a human tumor cell strain and
nonmalignant mouse and hamster fibroblastsin culture, and these effects
compared with those of phencyclidine 1. Investigation of these compounds in
mice showed significantly less toxicity and enhanced anesthetic effect of
the adamantyl derivatives 2a-b than of phencyclidine itself.
Keywords: phencyclidine, adamantylamine derivatives, synthesis, biological activity, cytotoxicity, cell-proliferation inhibition, anesthetic effect
Title: Synthesis and Photochemistry of
4-Methylene-2-protoadamantanone
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Pavlović, Dražen (139616)
- Šindler-Kulyk, Marija (47004)
Journal: Journal of Organic Chemistry
Number: 1
ISSN: 0022-3263
Volume: 58
Year: 1993
Pages: from 252 to 254
Number of references: 14
Language: engleski
Summary: 4-Methylene-2-protoadamantanone (4) has been prepared in
50%overall yield starting from 2-protoadamantenone, and itsphotochemical
reactions have been studied under direct andacetone-sensitized irradiation.
Irradiation of 4 in acetoneproceeds smoothly to give
1-(3-oxobutyl)-2-adamantanone (9) as amajor product (95% by GC). The
formation of 9 can be explainedvia a photoinitiated anti-Markovnikov
addition of acetonylradical to the double bond of the beta,gama-unsaturated
ketone 4.
Keywords: 4-Methylene-2-protoadamantanone, synthesis, photochemistry and mechanism
Title: Deuterium Isotope Effects on Nuclear Shielding. Cross-Ring
Effects in Rigid Cyclic Molecules
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Vinković, Vladimir (71214)
- Chyall, L.J.
- Gassman, P.G.
Journal: Magnetic Resonance in Chemistry
Number: 10
ISSN: 0749-1581
Volume: 31
Year: 1993
Pages: from 903 to 905
Number of references: 12
Language: engleski
Summary: Deuterium isotope effects on C-13 NMR chemical
shifts,(2H/1H)n delta(C 13), of 2-methylene-d2-adamantane,
4-methylene-d2-2-adamantanone and 6-methylene-d2-2-adamantanone are
presented. Long-range effects (4 delta, 5 delta and 6 delta) in a range
from 5 to -23 ppb were observed. The results for 5 delta and 6 delta are
explained in terms of cross-ring field effects resulting from the change of
dipole due to deuterium substitution.
Keywords: C-13 NMR, 2-methylene-d2-adamantane derivatives, deuterium isotope shifts
Title: Photochemical Behaviour of 4-Methylene-2-adamantanone, an
Exocyclic beta,gama-Unsaturated Ketone
- Authors:
- Mlinarić-Majerski, Kata (27342)
- Pavlović, Dražen (139616)
- Veljković, Jelena (18061)
- Šindler-Kulyk, Marija (47004)
Journal: Croatica Chemica Acta
Number: 2
ISSN: 0011-1643
Volume: 66
Year: 1993
Pages: from 385 to 392
Number of references: 14
Language: engleski
Summary: The photochemistry of 4-methylene-2-adamantanone (1) was
studied in different solvents and under direct and sensitized irradiation.
Depending on the conditions, beta,gama-unsaturated ketone 1 underwent
reactions characteristic of isolated ketones or alkenes. Direct irradiation
of 1 in benzene afforded a mixture of 2-methylenenoradamantane (11) and
4-methylenebicyclo(3.3.1)non-2-en-7-carbaldehyde (12). Irradiation of 1 in
benzene in the presence of benzophenone gave oxetanes 10, while the major
products in acetone sensitized photolysis were identified as syn- and
anti-4-(3-oxobutyl)-2-adamantanones (8). In protic solvent (ethanol), 1
reacted smoothly to give ketal 13. The photochemical reactions that proceed
through intramolecular interactions were not observed.
Keywords: 4-Methylene-2-adamantanone, photochemical reactions - direct and sensitized irradiation
Title: Polynitropolycyclic Cage Compounds
- Authors:
- Škare, Danko (94313)
- Mlinarić-Majerski, Kata (27342)
Journal: Kemija u industriji
Number: 8
ISSN: 0022-9830
Volume: 42
Year: 1993
Pages: from 267 to 285
Number of references: 118
Language: hrvatski
Summary: This paper presents the synthesis of polynitroadamantane
derivatives as well as the synthetic strategies of the strained molecules
such as nitro derivatives of cubane, bishomocubane,trishomocubane,
pentaprismane and its homologues and peristylanes.
Keywords: polynitropolycyclic cage compounds, derivatives of adamantane, cubane, homocubane, pentaprismane, peristylane, high-energy compounds
Title: n-pi-Interactions in Polycyclic Unsaturated Ketones:
Photoelectron Spectroscopic Study
- Authors:
- Kovač, Branka
- Novak, I.
- Mlinarić-Majerski, Kata
- Vinković, Marijana (117772)
- Kaselj, Mira (139620)
Journal: Journal of Organic Chemistry
Number: 11
ISSN: 0022-3263
Volume: 59
Year: 1994
Pages: from 3033 to 3036
Number of references: 17
Language: engleski
Summary: HeI photoelectron spectra (PE) of several
beta,gama-unsaturated polycyclic ketones, their parent ketones, and alkenes
have been measured. The assignment of spectra is based on semiempirical MO
calculations (PM3 method) and empirical arguments. Endo-derivatives showed
larger HOMO/SHOMO band separation than exo-cyclic unsaturated ketones. The
results of MO calculations are in good agreement with this general trend.
Strikingly different photochemical transformations and pi* = n electronic
transition intensities, exhibited by the two groups of compounds, can be
rationalized within the framework of exygen lone pair -- pi bond
interactions.
Keywords: n,pi-interactions, polycyclic unsaturated ketones, photoelectron spectroscopy
Title: Isomerization of Exocyclic Double Bonds. A Comparison of
Homoadamantyl vs Protoadamantyl Derivatives
- Authors:
- Mlinarić-Majerski, Kata
- Vinković, Marijana (117772)
- Fry, James L.
Journal: Journal of Organic Chemistry
Number: 3
ISSN: 0022-3263
Volume: 59
Year: 1994
Pages: from 664 to 667
Number of references: 19
Language: engleski
Summary: A study of the isomerization of a series of
methylenecycloalkanes in the presence of p-toluenesulfonic acid revealed
that the endo-isomers are always more stable than the exo-isomers. This
work has also been extended to the study of double-bond migration in the
rigid polycyclic molecules, such as protoadamantane and homoadamantane
derivatives.
Keywords: isomerization, exocyclic double bond, homoadamantyl derivatives, protoadamantyl derivatives
Title: Synthesis and X-Ray Structures of New Macrocyclic
Thioethers
- Authors:
- Mlinarić-Majerski, Kata
- Pavlović, Dražen (139616)
- Luić, Marija
- Kojić-Prodić, Biserka (21602)
Journal: Chemische Berihte
ISSN: 0009-2940
Volume: 127
Year: 1994
Pages: from 1327 to 1329
Number of references: 9
Language: engleski
Summary: 4,6:12,14-Di(1,3-adamantano)-1,9-dithiacyclohexadecane (1),
4,6:12,14:20,22-tri(1,3-adamantano)1,9,17-trithiacyclotetracosane (2), and
5,7:14,16-di(1,3-adamantano)-1,2,10,11-tetrathiacyclooctadecane (3) have
been obtained by intermolecular cyclization of
1,3-bis(2-bromoethyl)adamantane (4) with thioacetamide using a
high-dilution technique. The reaction is concentration-dependent. The
crystal structures of 1, 2 and 3 have been determined by single-crystal
X-ray diffraction.
Keywords: macrocyclic thioethers / Adamantane as a building block
Title: 1,2-Methanoadamantane: A Molecule with a Twist Bent sigma
Bond
- Authors:
- Mlinarić-Majerski, Kata
- Kaselj, Mira (139620)
Journal: Journal of Organic Chemistry
Number: 16
ISSN: 0022-3263
Volume: 59
Year: 1994
Pages: from 4362 to 4363
Number of references: 17
Language: engleski
Summary: The reaction of 1-(chloromethyl)-2-bromoadamantane with
sodium leads to ring closure to the higherto unknown 1,2-methanoadamantane
(1). Reactivity studies of 1 provide strong evidence for the existence of a
twist bent sigma bond.
Keywords: 1,2-methanoadamantane, twist bent sigma bond
Title: Synthesis and Reactivity Studies of
2,4-(Dimethylmethano)-2,4-didehydroadamantane: A Comparison with an
Unsubistituted Analogue
- Authors:
- Mlinarić-Majerski, Kata
- Šafar-Cvitaš, Dunja (46253)
- Veljković, Jelena (18061)
Journal: Journal of Organic Chemistry
Number: 9
ISSN: 0022-3263
Volume: 59
Year: 1994
Pages: from 2374 to 2380
Number of references: 33
Language: engleski
Summary: We prepared 2,4-(dimethylmethano)-2,4-didehydroadamantane
(1), a gem-dimethyl/3.1.1/propellane, and systematically examined its
chemical behavior in relation to its unsubstituted analogue
2,4-methano-2,4-didehydroadamantane (2). Propellane 1 is thermally more
stable than 2, but its reactivity is considerably greater than that of 2.
It is highly reactive toward electrophiles and free radicals. Propellane 1
also reacts with alcohols, dienes and oxygen but is less susceptible to
polymerization than 2. Enhanced chemical reactivity of
dimethyl/3.1.1/propellane 1, with respect to its unsubstituted analogue 2,
is in accord with an increase in nucleophilicity of its central bond due to
electron donation of the methyl groups.
Keywords: gem-dimethyl/3.1.1/propellane, reaction with elektrophiles and free radicals
Title: Onset of Anh Hyperconjugation in the Transition State of
Carbonyl Addition by Deactivation of Periplanar Vicinal Bonds
- Authors:
- Kaselj, Mira (139620)
- Adcock, James L.
- Luo, Huimin
- Zhang, Huqiu
- Li, Haifang
- le Noble, William J.
Journal: Journal of American Chemical Society
Number: 27
ISSN: 0002-7863
Volume: 117
Year: 1995
Pages: from 7088 to 7091
Number of references: 16
Language: engleski
Summary: The previously observed preferential syn delivery of
hydride anion in the reduction of the carbonyl group of
5-fluoroadamantan-2-one is inverted if the identities of all hydrogen and
fluorine atoms are reversed. A similar and somewhat smaller alteration is
observed in the reduction of 5-chloroperfluoroadamantan-2-one. The
interpretation is that the periplanar bonds are then no longer capable of
stabilizing the transition state by electron donation, and instead do so by
accepting electron density from the incipient bond into the sigma*
orbitals. The configuration of the reduction products were deduced from
their 19F NMR spectra by means of a chemical shift additivity procedure.
Keywords: Anh hyperconjugation, 5-fluoroadamantan-2-one, 5-chloroperfluoroadamantan-2-one
Title: Nature of the highest occupied molecular orbitals of
trans- and cis-bicyclo/4.1.0/hept-3-enes
- Authors:
- Gassman, P.G.
- Mlinarić-Majerski, Kata
- Kovač, Branka
- Chen, Han
- Dixon, D.A.
Journal: Journal of Physical Organic Chemistry
ISSN: 0894-3230
Volume: 8
Year: 1995
Pages: from 149 to 158
Number of references: 26
Language: engleski
Summary: Photoelectron spectra of trans-bicyclo/4.1.0/hept-3-ene and
two methyl derivatives, 1-3, and cis-bicyclo/4.1.0/hept-3-ene and three of
its derivatives, 4-7, were measured. Ab initio molecular orbital (MO) and
density functional theory (DFT) calculations were preformed on these
compounds. The combination of the experimental and theoretical results
clearly shows that the HOMO of the trans-bicyclo/4.1.0/hept-3-enes is
localized in the region of the "twist" bent sigma bond whreas for the
cis-bicyclo/4.1.0/hept-3-enes the HOMO is localized in the region of the pi
bond of the six-membered ring.
Keywords: trans-bicyclo/4.1.0/hept-3-ene derivatives, photoelectron spectra, twist bent sigma-bond
Title: Adamantyl phencyclidine - a potential effective
radioprotector
- Authors:
- Ferle-Vidović, Ana (11656)
- Petrović, Danilo (36926)
- Šuman, Lidija
- Škare, Danko (94313)
- Mlinarić-Majerski, Kata
- Kaselj, Mira (139620)
- Lasić, Mila
Journal: Periodicum Biologorum
Number: 1
ISSN: 0031-5362
Volume: 97
Year: 1995
Pages: from 41 to 44
Number of references: 11
Language: engleski
Summary: The compound phencyclidine
/1-(1-phenyl-cyclohexyl)piperidine/ (PCP) has been in use in veterinary
medicine because of its anestetic and analgesic properties for a rather
long time, but is toxicity always was a limiting factor, and that was the
reason that it was never accepted in human medicine. The adamantyl analogue
of phencyclidine (Ad-PCD) proved to be less toxic than phencyclidine it
self. We have tested radioprotective effects of PCP and Ad-PCP in
gamma-irradiated cultured cells and in mice. From our results it can be
calcuded that this adamantyl analog of phencyclidine has reduced toxicity
and increased radioprotection in cells and mice and therefore deserves
attention and might be interesting for further investigation.
Keywords: Phencyclidine, adamantyl derivate, radioprotection mice, culture cells
Title: Acid-Catalysed Rearrangement of
Tetracyclo/4.3.0.02,9.04,8/nonane Skeleton to Substituted Brendene
Derivatives
- Authors:
- Mlinarić-Majerski, Kata
- Kragol, Goran
- Šindler-Kulyk, Marija (47004)
- Pavlović, Dražen (139616)
Journal: Liebigs Annalen
ISSN: 0947-3440
Volume: 116
Year: 1995
Pages: from 1885 to 1889
Number of references: 18
Language: engleski
Summary: The synthesis of 2-exo-substituted brendene derivatives 3a,
5a and 6 as well as 2,5-disubstituted brendene derivative 7 is described,
starting from the readily available tetracyclo/4.3.0.02,9.04,8/nonanone 1.
The cationic rearrangement reactions of tetracyclic skeleton of 1 and 2
have been studied. The mechanism of these reactions is discussed. The
preparation of inaccessible exo-alcohol 2a by reduction of keton 1 is
presented
Keywords: 2,-exo-substituted brendene derivatives, 2,5-disubstituted brendene derivatives, cyclopropylcarbinyl cation
Title: A vibrational assignemnt of adamantane and some of its
isotopomers. Empirical versus scaled semiempirical force field
- Authors:
- Bistričić, L.
- Baranović, Goran
- Mlinarić-Majerski, Kata
Journal: Spectrochimica Acta
ISSN: 0584-8539
Year: 1995
Pages: from 0000 to 0000
Number of references: 16
Language: engleski
Summary: Raman and infrared spectra of adamantane-do and several of
its isotopomers (adamantane-1-d1, adamantane-2-d1 and adamantane-2,2-d2)
have been recorded and assigned using the valence empirical force field and
isotopic frequency shifts. Few inactive fundamentals of adamantane-do were
located by means of their activity in either the low-symmetry isotopomers
or the low-temperature phase. The vibrational spectrum of adamantane-d16
had to be reinterpreted. The force field obtained from the semiempirical
AM1 parametrization was scaled using the vibrational assignments for
adamantane-do, -d16 and -1-dy. The two force fields were compared. Both
reproduced the observed frequencies with practically the same average error
of 16 cm-1. However, the number of parameters in the scaled semiempirical
force field is only nine compared with 27 of the empirical force fiels.
Keywords: adamantane, force field, isotopomer
Information: svibor@znanost.hr
