POLISH JOURNAL OF CHEMISTRY
Volume 72 Number 1 January 1998
Pages 1-150


CONTENTS

Page

REVIEW ARTICLE
1 Recent Developments in the Synthesis of -Hydroxy-ß-amino Acids
— Andruszkiewicz R.
INORGANIC CHEMISTRY
49 The CuGaSe2-HgSe and CuInSe2-HgSe Systems
— Olekseyuk I.D., Parasyuk O.V. and Galka V.O.
55 Spectroscopic Studies of Zn(II) Halides Complexes with 5,7-Disubstituted Derivatives of 1,2,4-Triazolo-[1,5a]-pyrimidine
— Szlyk E., Grodzicki A., Pazderski L. and Sitkowski J.
ORGANIC CHEMISTRY
61 Synthesis of Some New Pyrimidines, Thienopyrimidines and Thiopyranopyrimidines
— Assy M.G., Amer A.M., El-Bahaie S. and Halima E.A.
66 Trapping of Thiocarbonyl Ylides with NH-Azoles; A Novel Route to N-Substituted Azoles
— Mloston G., Gendek T. and Heimgartner H.
73 Synthesis and X-ray Studies of Derivatives of 1,2,4-Triazolidine-3-thiones
— Korzycka L., Glowka M. and Janicka J.
78 Synthesis of Some 5-Amino-2-methyl-4-nitro-1-phenacylimidazoles
— Sobiak S.
84 Synthesis of Hepatitis C Virus Protein Fragments and Evaluation of Their Immunogenicity
— Karawajczyk B., Mackiewicz Z., Kunikowska D., Dziadziuszko H., Dera-Tomaszewska B., Glosnicka R. and Kupryszewski G.
89 Reaction of Benzo[h]naphthyridine N-Oxides with Phenyl Isocyanate
— Bachowska B. and Zujewska T.
93 Synthesis and Reactions of Organic Compounds with a Nitrogen Atom. Part XIII. Reaction of alpha- and ß-Pyronene with Bis(p-toluenesulfonyl)selenodiimide
— Scianowski J. and Uzarewicz A.
PHYSICAL CHEMISTRY
99 Kinetics and Mechanism of Oxidation of L-Phenylalanine by Alkaline Permanganate
— Panari R.G., Chougale R.B. and Nandibewoor S.T.
108 Kinetics of the Reaction of 2,3,5,6-Tetrachloro-1,4-benzoquinone with Imidazole in Acetonitrile and Benzene
— Dworniczak M., Przybyszewska M. and Jarczewski A.
113 A Kinetic Study of the Base-Catalyzed Dimerization of 5(4H)-Oxazolones
— Mazurkiewicz R., Pierwocha A.W. and Fryczkowska B.
122 Kinetics of Oxidation of Oxine by Pyridinium Dichromate
— Palaniappan AN., Bharathi K. and Sekar K.G.
127 Micelle Formation in Aqueous NaBr Solutions of Alkyltrimethylammonium Bromides
— Zielinski R.
COMMUNICATIONS
137 Acid-Base Equilibrium in Fused Ethylammonium Chloride
— Wiecek B.
141 Reactions of n-Butanol in the Presence of Dehydrogenating Iron Catalyst
— Grabowska H. and Klimkiewicz R.
146 Differential Hygrometric Analysis (DHA) - A New Quick Method for Investigation of the Interaction between Water Vapour and Solids
— Baranowski B. and Lunden A.
ERRATA
149 Kinetic Network for Oxidative Dehydrogenation of Propane on Vanadia-Titania Catalysts
— Sloczynski J., Grabowski R., Wcislo K. and Grzybowska-Swierkosz B.
150 IUPAC Recommendations on Nomenclature and Symbols.


ABSTRACTS


1-48

Recent Developments in the Synthesis
of -Hydroxy-ß-amino Acids

by R. Andruszkiewicz
Department of Pharmaceutical Technology and Biochemistry, Technical University of Gdansk, 80-952 Gdansk, Poland

(Received August 7th, 1997; revised manuscript September 19th, 1997)

Naturally occurring compounds containing -hydroxy-ß-amino acids have been presented in the first part of this review. The second part gives a summary of the more recent developments in the synthesis of enantiomerically and diastereomerically pure -hydroxy-ß-amino acids. Application of new strategies useful in the preparation of peptides with -hydroxy-ß-amino acids is also presented.

49-54

The CuGaSe2-HgSe and CuInSe2-HgSe Systems

by I.D. Olekseyuk, O.V. Parasyuk and V.O. Galka
Department of Inorganic and Physical Chemistry, Volyn State University,
Voli av. 13, Lutsk 263009, Ukraine

(Received April 29th, 1997; revised manuscript August 18th, 1997)

Phase diagrams in the CuGaSe2-HgSe and CuInSe2-HgSe systems have been constructed using differential thermal, X-ray phase and microstructural analyses. The CuGaSe2-HgSe system is of the peritectic type. Solid solutions of the constituent components have been found and their limit compositions have been established. They contain 0-3 and 63-100 mol.% HgSe at 870 K. The CuInSe2-HgSe system is of the first type, due to Roozeboom classification. A continuous range of solid solutions exists between HgSe and the high-temperature ß-modification of CuInSe2. The solid solutions are created on the basis of -CuInSe2 which contains up to 7 mol.% HgSe at 870 K.

55-60

Spectroscopic Studies of Zn(II) Halides Complexes
with 5,7-Disubstituted Derivatives of
1,2,4-Triazolo-[1,5a]-pyrimidine

by E. Szlyk1, A. Grodzicki1, L. Pazderski1 and J. Sitkowski2
1Department of Chemistry, Nicholas Copernicus University, 87-100 Torun, Poland
2Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland

(Received May 28th, 1997; revised manuscript September 19th, 1997)

Complexes of ZnX2 (X = Cl, Br, I, SCN) with 5,7-dimethyl-1,2,4-triazolo-[1,5a]-pyrimidine, 5,7-diphenyl-1,2,4-triazolo-[1,5a]-pyrimidine and 5,7-di-tert-butyl-1,2,4-tri-
azolo-[1,5a]-pyrimidine were prepared and characterized by IR (100-4000 cm-1) and 1H, 13C, 15N NMR spectroscopies. Spectral data suggest pseudo-tetrahedral configuration around Zn(II) atom with N-3 bonded heterocycles. Halides and thiocyanates (N bonded) are in terminal positions.

61-65

Synthesis of Some New Pyrimidines, Thienopyrimidines and Thiopyranopyrimidines

by M.G. Assy, A.M. Amer, S. El-Bahaie and E.A. Halima
Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt

(Received November 20th, 1996; revised manuscript July 7th, 1997)

Isothiocyanate 1 reacted with enaminone 2 to give thioamide 3 that cyclized by sodium hydroxide to pyrimidine 4 but cyclized by bromine to give isothiazole 5, pyrimidine 4 was transformed into thiopyranopyrimidines 7, 9 or 11 upon respective reaction with benzaldehyde, maleic acid, or maleic anhydride. Aminative cyclization of 4 yielded isothiazolopyrimidine 13. Reaction of 4 and ethyl bromoacetate or phenacyl bromides afforded thienopyrimidines 15a-b respectively. Oxidation of 4 yielded oxopyrimidine 16.

66-72

Trapping of Thiocarbonyl Ylides with NH-Azoles;
A Novel Route to N-Substituted Azoles

by G. Mloston1, T. Gendek1, and H. Heimgartner2
1Department of Organic and Applied Chemistry, University of Lodz,
Narutowicza 68, PL-90-136 Lodz, Poland
2Organisch-chemisches Institut der Universitaet Zuerich,
Winterthurerstrasse 190, CH-8057 Zuerich, Switzerland

(Received August 11th, 1997)

Thermal decomposition of 2,5-dihydro-1,3,4-thiadiazoles (1) in the presence of imidazole, pyrazole, 3-phenylpyrazole, and 1,2,4-triazole, respectively, yielded S,N-acetals of type 4. Interception of initially formed thiocarbonyl ylide 2 by the NH-azole is proposed as the reaction mechanism. Treatment of the S,N-acetals 4 with Raney-Ni gave N-substituted azoles 6.

73-77

Synthesis and X-ray Studies of Derivatives of
1,2,4-Triazolidine-3-thiones

by L. Korzycka1, M. Glowka2 and J. Janicka2
1Department of Pharmaceutical Chemistry and Drug Analysis, Medical University of Lodz,
Muszynskiego 1, 90-151 Lodz, Poland
2Institute of General and Ecological Chemistry, Technical University of Lodz,
Zwirki 36, 90-924 Lodz, Poland

(Received June 20th, 1997; revised manuscript September 1st, 1997)

Reactions of 2,4-disubstituted thiosemicarbazides with acetone catalyzed by sulfuric acid gave cyclic 1,2,4-triazolidine-3-thione derivatives. The same reaction with no catalyzer gave open-chain compounds. Synthesis and X-ray studies of some 1,2,4-triazolidine-3-thiones are described.

78-83

Synthesis of Some 5-Amino-2-methyl-4-nitro-
-1-phenacylimidazoles

by S. Sobiak
Department of Chemical Technology of Drugs, Faculty of Pharmacy,
K. Marcinkowski University of Medical Sciences, 60-780 Poznan, Poland
E-mail: sobiakst@chem.amu.edu.pl

(Received June 13th, 1997; revised manuscript September 5th, 1997)

Reaction of 4(5)-bromo-2-methyl-5(4)-nitroimidazole with phenacyl bromide derivatives gave two isomers: 4-bromo-5-nitroimidazoles (4a-e) and 5-bromo-4-nitroimidazoles (5a-e). Compounds 5a-e were treated with cyclic secondary amines to afford expected 5-amino-4-nitroimidazole derivatives 6a-c - 10a-b.

84-88

Synthesis of Hepatitis C Virus Protein Fragments
and Evaluation of Their Immunogenicity

by B. Karawajczyk1, Z. Mackiewicz1, D. Kunikowska2, H. Dziadziuszko2,
B. Dera-Tomaszewska2, R. Glosnicka2 and G. Kupryszewski1
1Faculty of Chemistry, University of Gdansk, 80-952 Gdansk, Poland
2Institute of Maritime and Tropical Medicine, 81-519 Gdynia, Poland

(Received August 7th, 1997; revised manuscript September 11th, 1997)

Three polypeptide fragments of Hepatitis C virus protein (130-140)C, (133-142)C and (1406-1415)NS3 were synthesized using the solid-phase method. The immunogenicity of the peptides was tested on rabbits. All the peptides studied revealed humoral and cell response.

89-92

Reaction of Benzo[h]naphthyridine N-Oxides
with Phenyl Isocyanate

by B. Bachowska and T. Zujewska
Institute of Chemistry, Pedagogical University, PL - 42-201 Czestochowa, Poland

(Received June 30th, 1997; revised manuscript September 12th, 1997)

Benzo[h]naphthyridine N-oxides reacted with phenyl isocyanate in dimethylformamide to give carbamic acid derivative at room temperature or anilino derivatives at 150oC. The process proceeded via 1,3-dipolar cycloaddition followed by aromatization with N-O bond cleavage and loss of CO2 at higher temperature.

93-98

Synthesis and Reactions of Organic Compounds
with a Nitrogen Atom. Part XIII. Reaction of alpha-
and ß-Pyronene with Bis(p-toluenesulfonyl)selenodiimide

by J. Scianowski and A. Uzarewicz
Faculty of Chemistry, Nicolaus Copernicus University, 87-100 Torun, Poland

(Received June 30th, 1997; revised manuscript September 17th, 1997)

Toluenesulfonamidation of -pyronene (1,5,5,6-tetramethyl-1,3-cyclohexadiene) afforded two toluenesulfonamides:N,N'-(1',5',5',6'-tetramethyl-3'-cyclohexen-1',2'-diyl)di- toluenesulfonamide (9) and 4-methyl-N-(4',5',6',6'-tetramethyl-2',4'-cyclohexadien-1'—yl)benzenesulfonamide (12). Toluenesulfonamidation of ß-pyronene (1,2,6,6-tetramethyl-1,3-cyclohexadiene) gave N,N'-(3',4',5',5'-tetramethyl-3'-cyclohexen-1',2'-diyl) ditoluenesulfonamide (16). Allylic mono- and ditoluenesulfonamides 9, 12, 16 were reduced by sodium in liquid ammonia to corresponding allylic mono- and diamines 17,18 i 19.

99-107

Kinetics and Mechanism of Oxidation of L-Phenylalanine by Alkaline Permanganate

by R.G. Panari, R.B. Chougale and S.T. Nandibewoor
P.G. Department of Studies in Chemistry, Karnatak University, Dharwad 580 003, India

(Received April 7th, 1997; revised manuscript June 23th, 1997)

The kinetics of oxidation of L-phenylalanine by alkaline permanganate follows the rate law -d[MnO4-]/dt   =  {k K[L-phenylalanine][MnO4- ]}/{1+K[L-phenylalanine]} where K is the formation constant for the complex between L-phenylalanine and permanganate and k is the decomposition rate constant. The data suggest that the oxidation of L-phenylalanine proceeds via the formation of a complex between L-phenylalanine and permanganate which decomposes slowly, followed by a fast reaction between the free radical of L-phenylalanine and another molecule of permanganate to give the products. The reaction constants involved in the mechanism are derived. There is a good agreement between the observed and calculated rate constants at varying conditions of experiments. The activation parameters are computed with respect to the slow step of the mechanism.

108-112

Kinetics of the Reaction of 2,3,5,6-Tetrachloro-1,4-
-benzoquinone with Imidazole in Acetonitrile and Benzene

by M. Dworniczak, M. Przybyszewska and A. Jarczewski
Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland

(Received May 22nd, 1997; revised manuscript July 28th, 1997)

Nucleophilic vinylic substitution of 2,3,5,6-tetrachloro-1,4-benzoquinone by imidazole in acetonitrile and benzene has been studied spectrophotometrically. The reaction product is the diaminodichlorosubstituted quinone. The values of the activation parameters indicate that there is a considerable charge separation in the transition state. The reaction mechanism is discussed.

113-121

A Kinetic Study of the Base-Catalyzed
Dimerization of 5(4H)-Oxazolones

by R. Mazurkiewicz1, A.W. Pierwocha1 and B. Fryczkowska2
1Institute of Organic Chemistry and Technology, The Silesian Technical University,
Krzywoustego 4, 44-100 Gliwice, Poland
2Textile Institute, Technical University of Lodz, Branch in Bielsko-Biala,
Plac Fabryczny 5, 43-300 Bielsko-Biala, Poland
e-mail: romanm@zeus.polsl.gliwice.pl

(Received July 31st, 1997)

The effects of the substituent at position-2 and kind of the base on the rate of the base-catalyzed dimerization of 5(4H)-oxazolones have been investigated. The electron-donating and strong steric effect of the substituent at position-2 reduce markedly the proclivity of 5(4H)-oxazolones to dimerization. The following catalytic activity sequence of the bases has been found: DBU >> Et3N >> (i-Pr)2EtN.

122-126

Kinetics of Oxidation of Oxine by
Pyridinium Dichromate

by AN. Palaniappan*, K. Bharathi and K.G. Sekar
Department of Chemistry, Annamalai University, Annamalainagar - 608 002, India

(Received June 20th, 1997; revised manuscript August 11th, 1997)

The kinetics of oxidation of 8-hydroxyquinoline (oxine) by pyridinium dichromate has been studied in 60% acetic acid-water (v/v) medium. The reaction order is one with respect to oxidant, second with respect to the substrate and zero with respect to hydrogen ion concentration. Decrease of the dielectric constant of the medium, reduces the rate of the reaction. Increase in ionic strength has no effect on the reaction rate. The reaction does not induce the polymerization of acrylonitrile. From the kinetic data obtained, the activation parameters have been calculated and a plausible mechanism has been proposed.

127-136

Micelle Formation in Aqueous NaBr Solutions
of Alkyltrimethylammonium Bromides

by R. Zielinski
Department of General Technology, Faculty of Commodity Science, Poznan
University of Economics, Aleja Niepodleglosci 10, 60-967 Poznan, Poland

(Received January 31st, 1997; revised manuscript October 8th, 1997)

Sound velocity in aqueous solutions of alkyltrimethylammonium bromides with alkyl chains of octyl, decyl, dodecyl and tetradecyl has been measured as a function of surfactant and NaBr concentrations at 25oC. The critical micelle concentrations, CMC, were determined from intersections of two straight line portions of the surfactant concentration dependence of sound velocity in the solutions. CMC decreases with the increase of ionic strength, following the Corrin-Harkins equation. The standard free energy of micelle formation was estimated from the CMC at different NaBr concentrations. It was presented as a sum of increments of the methylene and the polar head groups at each NaBr concentration. The methylene group contribution varies with NaBr concentration from -1.81 kJ/mol in water to -2.95 kJ/mol at salt concentrations higher than 0.5 m NaBr.

137-140

Acid-Base Equilibrium in Fused
Ethylammonium Chloride

by B. Wiecek
Faculty of Chemistry, University of Wroclaw, 50383 Wroclaw, Poland

(Received June 9th, 1997; revised manuscript October 3rd, 1997)

141-145

Reactions of n-Butanol in the Presence
of Dehydrogenating Iron Catalyst

by H. Grabowska and R. Klimkiewicz
Institute of Low Temperature and Structure Research, Polish Academy of Sciences,
P.O. Box 937, 50-950 Wroclaw 2, Poland

(Received June 18th, 1997; revised manuscript October 10th, 1997)

146-148

Differential Hygrometric Analysis (DHA) - A New Quick Method for Investigation of the Interaction
between Water Vapour and Solids

by B. Baranowski1 and A. Lunden2
1Institute of Physical Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
2Department of Physics, Chalmers University of Technology, S-41296 Goeteborg, Sweden

(Received September 4th, 1997; revised manuscript October 16th, 1997)

149

ERRATA Kinetic Network for Oxidative Dehydrogenation of Propane
on Vanadia-Titania Catalysts

by J. Sloczynski, R. Grabowski, K. Wcislo and B. Grzybowska-Swierkosz
[Vol. 71, 1585-1593 (1997)]

150

IUPAC RECOMMENDATIONS ON NOMENCLATURE AND SYMBOLS

  • Provisional Nomenclature Report from Commission V.5
    Analytical Aspects of Chemically Modified Electrodes:
    Classification, Critical Evaluation and Recommendations
    (IUPAC Recommendations 1977)


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