Chromium(III) and oxovanadium (IV) complexes of some urea derivatives

Summary The preparation of eight new complexes of Cr^III and VO^IV with urea derivatives is reported here. The ligands used were 2-imidazolidinone (ethyleneurea, EU),N,N'-dimethyl-2-imidazolidinone (N,N -dimethylethyleneurea, DMEU), 2-imidazolidinethione (ethylenethiourea, ETU), andN, N, N, N -tetramethyl-2-imidazolidone (tetramethylurea, TMU). The previously reported complex VOCl₂(TMU)₂ was also prepared. All nine complexes were investigated with regard to conductimetry as well as visible and i.r. spectroscopy. All carbonyl-containing complexes exhibit a metal-oxygen bond, whereas in ETU complexes a metal-nitrogen bond seems to be favoured.     

Synthesis and Characterization of Solid Coordination Complexes of Diamides for Uranium(VI) and Thorium(IV)

Five kinds of solid coordination complexes of uranium(VI) and thorium(IV) with the diamide (N,N,N,N-tetrabutylmalon-amide (TBMA), N,N,N,N-tetrabutylsuccinylamide (TBSA), N,N,N,N-tetrabutylglutaramide (TBGA), N,N,N,N-tetrabutyl-adipicamide (TBAA)) were synthesized. All these complexes of UO₂(NO₃)₂·TBMA, UO₂(NO₃)₂· TBSA, [UO₂(NO₃)₂·(TBGA^1/2)₂] _x , UO₂(NO₃)₂·TBAA and Th(NO₃)₄·2TBMA were characterized by elemental analysis, UV spectra, IR spectra and ¹³C NMR spectra. The coordination form and proposed structures of the complexes are also discussed.     

Umsetzungen des Diphenylphosphinsäureanilids

Zusammenfassung Diphenylphosphinsäureanilid-kalium wurde in Lösung von Dioxan erhalten und mit Alkylhalogeniden zu Diphenylphosphinsäure-alkylaniliden umgesetzt. Mit Methylenjodid entsteht N,N-Bis-[diphenylphosphinsäure]-N,N-diphenylmethylendiamid, während mit Äthylenbromid Acetylen und Diphenylphosphinsäureanilid erhalten wird. Mit Ph₂P(O)Cl bzw. PhP(O)Cl₂ erhält man N,N-Bis-[diphenylphosphinsäure]-N-phenyl-amid bzw. Phenylphosphonsäure-N,N-diphenyl-N,N-bis-[diphenylphosphinsäure]-diamid.     

Syntheses and properties of mixed dinuclear copper(II) complexes with heterocyclic dithiocarbamates and a cyclic octadentate tertiary amine

Five new Cu^II complexes of general formula [Cu₂(Rdtc)tpmc](ClO₄)₃, (1)–(5), where tpmc and Rdtc ^– refer to N,N,N,N-tetrakis(2-pyridylmethyl)-1,4,8,11-teraazacyclotetradecane and piperidine- (Pipdtc), 4-morpholine- (Morphdtc), 4-thiomorpholine- (Timdtc), piperazine- (Pzdtc) or N-methylpiperazine- (N-Mepzdtc) dithiocarbamates, respectively, have been prepared. Elemental analyses, conductometric and magnetic measurements, u.v./vis, i.r., e.p.r. and mass spectroscopy have been employed to characterize them. The complexes adopt an exo coordination of Cu^II ions and tpmc. The dithiocarbamate ion joins both the sulphur and the copper atoms acting as a bridging ligand The presence of different heteroatoms in the piperidine ring influences the (C=N) and (C=S) vibrations which decrease in the order of the complexes: Pipdtc>N-Mepipdtc>Pzdtc>Morphdtc>Timdtc ligands. Attention has been paid to the detailed mechanism of the mass spectral fragmentation of the complexes. The g _eff factors of the complexes have been also estimated by e.p.r. spectra. Finally, the complexes obtained demonstrate microbiologycal activity against some bacteria.     

Palladium and platinum guanine complexes

Summary Reaction of [MCl₂(H₄Y)] or (H₆Y)[MCl₄] compounds (M = Pd or Pt; Y = EDTA, PDTA or CDTA) with guanine (Gu-H) in 0.5 M HCl yields new complexes MCl₂(Gu-H)(H₂O which have been characterized by elemental analyses in conjunction with electronic, i.r. and n.m.r. spectra. A dimeric structure with two bridging chloride ligands, including coordination of guanine through atom N(9), is proposed for both compounds.Abbreviations used in the paper EDTA 1,2-diaminoethane-N,N,N,N-tetraacetate - PDTA 1,2-diaminopropane-N,N,N,N-tetraacetate - CDTA trans-1,2-diaminocyclohexane-N,N,N,N-tetraacetate - Gu-H guanine - 9-EtGu-H 9-ethylguanine     

Cobalt(II) and nickel(II) chloride and bromide complexes of 2-(2′-methyl-8′-quinolyl)benzoxazole and 2-(2′ or 4′-methyl 8′-quinolyl)benzimidazole

Summary Cobalt(II) and nickel(II) halide complexes of the ligands 2-(2-methyl-8-quinolyl)benzoxazole (mqbo), 2-(2-methyl8quinolyl)benzimidazole (mqbi) and 2-(4-methyl-8-quinolyl)benzimidazole (mqbi) were synthesized and characterized by analytical, thermogravimetric, conductivity and magnetic data, and i.r. and electronic spectra.The ligands are bidentate N-donors yielding complexes where the coordination geometry depends on the metal ion and steric hindrance. All the cobalt complexes have formula [CoL₂X₂] and distorted tetrahedral geometry. Different types of nickel compounds were obtained: i) complexes of formula NiLX₂ · n H₂O (or EtOH) (L = mqbo or mqbi; n=0–1.5) which arepseudo-tetrahedral or five-coordinate and ii) complexes NiL₂X₂ · n H₂O (L = mqbi, n=3 or 4) where the metal is bound to four nitrogen atoms and the overall coordination geometry is tetragonal. The structural changes occurring after removal of water or alcohol from the complexes are also reported.     

New route for the synthesis of 2-thiouracil analogues of 3′-azido-2′,3′-dideoxy nucleosides

Summary Reaction of 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-pentofuranoside (5) with silylated 2-thiouracil and 5-alkoxy-2-thiouracils in the presence of trimethylsilyl trifluoromethanesulfonate afforded an anomeric mixture of the corresponding 3-azido-2,3-dideoxy-2-thiouridine derivatives with the -anomer as the main product. Deprotected nucleosides were obtained by treatment with tetrabutylammonium fluoride.

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Ein neuer Weg zur Synthese von 2-Thiouracil-Analogen von 3-Azido-2,3-dideoxy-Nucleosiden

Zusammenfassung Die Reaktion von 3-Azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-erythro-pentofuranosid (5) mit silyliertem 2-Thiouracil und 5-Alkoxy-2-thiouracil in Gegenwart von Trimethylsilyltrifluormethansulfonat ergab eine anomere Mischung der entsprechenden 3-Azido-2,3-dideoxy-2-thiouridin-Derivate, wobei das -Anomer das Hauptprodukt darstellte. Die ungeschützten Nucleoside wurden mittels Behandlung mit Tetrabutylammoniumfluorid erhalten.

     

Synthesis of some 5′-O-amino acid derivatives of uridine as potential inhibitors ofUDP-glucuronosyltransferase

Summary In an attempt to develop potential inhibitors ofUDP-glucuronosyltransferase, some 5-O-amino acid derivatives of uridine were synthesized. N-protectedL-amino acids were coupled at the 5-O-position of 2,3-O-isopropylideneuridine by esterification employing the method of symmetrical anhydrides in presence of 4-dimethylaminopyridine, 5-O-(N-benzyloxycarbonyl-O-tert.butyl-L-threonl)-23-O-isopropylideneuridine (1), 5-O-(N-tert.butyloxycarbonyl-O-benzyl-L-seryl)-2,3-O-isopropylideneuridine and (2), 5-O-(N-tert.butyloxycarbonyl-L-valyl)-2,3-O-isopropylideneuridine (3), and 5-O-(N-tert.butyloxycarbonyl-L-valyl)-2,3-O-isopropylideneuridine (4) were obtained in good yield after column chromatography on silica gel. The treatment of2 withTFA/CH₂Cl₂ (6:1) at room temperature for 30 min led to a selective removal of theBoc group without deblocking of the 2,3-O-isopropylidene group of uridine. Treatment of2 withTFA/H₂O (5:1) at room temperature for 1 h, however, released bothBoc and 2,3-isopropylidene groups. TheZ group of1 was deprotected by catalytic hydrogenolysis over 10% Pd/C/ammonium formate.

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Synthese von 5-O-Aminosäurederivaten des Uridins als potentielle Inhibitoren derUDP-Glukuronosyl-Transferase

Zusammenfassung In einem Versuch, potentielle Inhibitoren derUDP-Glukuronosyl-Transferase zu entwickeln, wurden einige 5-O-Aminosäurederivate des Uridins synthetisiert. N-GeschützteL-Aminosäuren wurden durch Veresterung mit der 5-O-Position des 2,3-isopropylidenuridins gekuppelt (Methode der symmetrischen Anhydride in der Gegenwart von 5-Dimethylaminopyridin). Solcherweise wurden 5-O-(N-Benzyloxycarbonyl-O-tert.butyl-L-threonly)-2,3-O-isopropylidenuridin (1), 5-O-(N-tert.Butyloxycarbonyl-O-benzyl-L-seryl)-2,3-O-isopropylidenuridin (2), 5-O-(N-tert.Butyloxycarbonyl-L-leucyl)-2,3-O-isopropylidenuridin (3) und 5-O-(N-tert.Butyloxycarbonyl-L-valyl)-2,3-O-isopropylidenuridine (4) nach Säulenchromatographie (Kieselgel) in guter Ausbeute hergestellt. Die Behandlung von2 mitTFA/CH₂Cl₂ (6:1) bei Zimmertemperatur (30 min) führte zu einer selektiven Abspaltung derBoc-Gruppe ohne Deblockierung der 2,3-O-Isopropylidengruppe des Uridins. Eine Behandlung von2 mitTFA/H₂O (5:1) bei Zimmertemperatur für 1 Stunde führte hingegen zur Abspaltung sowohl derBoc als auch der 2,3-O-Isopropylidengruppe. DieZ-Gruppe von1 wurde durch katalytische Hydrogenolyse auf 10% Pd/C/Ammoniumformiat abgespalten.

     

A Simplified version of the Pariser-Parr-Pople treatment of π-electron systems

The semi-empirical configuration interaction treatment due to Pariser and Parr and to Pople has been modified by reducing the set of electronic interaction integrals to ₁₁ and ₁₂ and by limiting the number of configurations to 10. Hückel MOs are used as basis functions. The dependence of the resonance integral _v on the interatomic distance R _v is simulated by making _v a quadratic function of the Hückel bond orders P _v .

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Zusammenfassung Eine Modifikation des semiempirischen CI-Verfahrens von Pariser, Parr und Pople wurde zur Behandlung von -Systemen herangezogen. Als Vereinfachung wurde der Grad der CI-Matrix auf zehn beschränkt und von den Elektronenwechselwirkungsintegralen nur ₁₁ und ₁₂ berücksichtigt. Hückel-MOs wurden als Basisfunktionen verwendet. Die Abhängigkeit des Resonanzintegrals _v vom interatomaren Abstand R _v wurde durch den Ansatz von _v als quadratische Funktion der Hückel-Bindungsordnung P _v angenähert.

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Résumé Le procédé semi-empirique de l'interaction de configuration selon Pariser, Parr et Pople a été modifié en réduisant l'ensemble des intégrales d'interaction électronique à ₁₁ et limitant le nombre des configurations à 10. Les fonctions de base sont des orbitales moléculaires selon Hueckel. La dépendance entre l'intégrale de résonance _v et la distance interatomique R _v est simulée en posant que _v est une fonction quadratique des ordres de liaisons P _v selon Hückel.

     

Darstellung von 2′,3′-Dideoxy-2′-hydroxymethyl-nucleosiden

Zusammenfassung Die Synthese von geschützten 2,3-Dideoxy-2-hydroxymethyl-nucleosiden wird beschrieben. Die durch ein Mehrstufenverfahren aus Isopropylidenglycerol erhaltenen Nucleoside können als Bausteine zur Darstellung von Oligonucleotiden verwendet werden, deren 2- und 5-Positionen über eine Etherbrücke verbunden sind.

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Synthesis of 2,3-dideoxy-2-hydroxymethyl nucleosides

Summary The synthesis of protected 2,3-dideoxy-2-hydroxymethyl nucleosides is presented. The nucleosides, obtained in a multi-step procedure starting from isopropylideneglycerol, may be used as building blocks for the synthesis of 2,5-ether linked oligonucleotides.

     

Syntheses and characterization of cobalt(II) and iron(III) complexes with the Schiff basesN-(o-hydroxybenzylidene)-2-aminobenzimidazole andN-(o-hydroxybenzylidene)-2(2′-aminophenyl)benzimidazole

Summary N-(o-hydroxybenzylidene)-2-aminobenzimidazole (HL) andN-(o-hydroxybenzylidene)-2(2-aminophenyl)benzimidazole (HL) react with CoX₂ (X=Cl, Br, or NCS) and FeCl₃ yielding complexes of general formulae [Co(HL)₂X₂], [Co(HL)₂X₂], [FeCl₂(HL)₂] [FeCl₄], and [FeCl₂(HL)₂][FeCl₄]. Moreover, it was possible to isolate the complexes [Co(HL)Br₂] [Co(L)Cl] and [Co(L)Cl]. The complexes were characterized by elemental analyses, i.r. and electronic spectroscopies and conductivity and magnetic measurements at different temperatures.     

Zur Mannich-Reaktion von Dihydro-6-methyl-2(1H)-pyrimidinonen

Zusammenfassung Dihydro-4,4,6-trimethyl-2(1H)-pyrimidinone reagieren mit Formaldehyd und sekundären bzw. primären Aminen zu 6-Dialkylaminoäthylidentetrahydro-2(1H)-pyrimidinonen bzw. Hexahydro-2(1H)-pyrido[4,3-d]Pyrimidinonen. Mit Succindialdehyd bzw. Glutardialdehyd und primären Aminen entstehen 5,7-Äthanohexahydro-2(1H)-pyrido[4,3-d]pyrimidinone bzw. Tetrahydro-6,8-propano-6H-pyrimido[1,6-c]pyrimidin-1(2H)-one. Die 6-Dialkylaminoäthylidentetrahydro-2(1H)-pyrimidinone geben mit Phenolen Tetrahydrospiro([1]benzopyran-2,4(1H)-pyrimidin)-2(3H)-one, mit cycl. -Dicarbonylverbindungen Hexahydrospiro([1]benzopyran-2,4(1H)-pyrimidin)-2,5(3H, 6H)-dione bzw. Tetrahydrospiro(2H,5H-pyrano[3,2-c][1]benzopyran-2,4(1H)-pyrimidin)-2(3H),5-dione bzw. mit Malonestern -(Tetrahydro-4,4-dimethyl-2-oxo-6-pyrimidyl)-äthylmalonester.Zusammenfassung Dihydro-4.4.6-trimethyl-2(1H)-pyrimidinones react with formaldehyde and sec. and prim. amines resp. to 6-dialkylaminoethylidentetrahydro-2(1H)-pyrimidinones and hexahydro-2(1H)-pyrido[4.3-d]pyrimidinones, resp. succindialdehyde and glutaraldehyde with primary amines give 5.7-ethanohexahydro-2(1H)-pyrido[4.3-d]pyrimidinones and tetrahydro6.8-propano-6H-pyrimido[1.6-c]pyrimidin-1(2H)-ones, resp. 6-Dialkylaminoethylidentetrahydro-2(1H)-pyrimidinones react with phenols to tetrahydrospiro([1]benzopyran-2.4(1H)-pyrimidin)-2(3H)-ones, with cyclic -dicarbonyl compounds to hexahydrospiro([1]benzopyran-2.4 (1H)-pyrimidin)-2,5 (3H), 6H)-diones and tetrahydrospiro(2H,5H-pyrano[3.2-c][1]benzopyran-2.4(1H)-pyrimidin)-2(3H),5-diones, resp., with malonates -(tetrahydro-4.4-dimethyl-2-oxopyrimidyl-6)-ethylmalonates.

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Mannich reaction with dihydro-6-methyl-2(1H)-pyrimidinones

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Herrn Prof. Dr.F. Kuffner zum 65. Geburtstag gewidmet.     

Studies on mixed ligand complexes,part III. Cobalt(III) heterochelates derived fromN,N′-tetramethylenebis(salicylideneimine),N,N′-ethylenebis(acetylacetoneimine) and bidentate OO and ON donor ligands

Summary The hydroxoaquo complex, Co(OH)(H₂O)(salbn) [salbnH₂ =N,N-tetramethylcnebis(salicylideneimine)] reacts with bidentate OO and ON donor ligands in ethanol at 100° to give hetcrochelate complexes of the type Co(AA)(salbn) (where AA = bidentate monobasic ligands such as picolinic acid, acetylacetone, tropolone,N-benzoylphenylhydroxyl-amine, acetoacetanilide, salicylaldehyde and 2-hydroxy-l-naphthaldehyde). Thecis-diammineN,N-ethylenebis(acetyl-acetoneimine)cobalt(lll)chloride reacts with bidentate ligands such as tropolonc to form the heterochelate complex Co(tropolone)(baen) [where baenH₂ =N,N-ethylenebis(acetyl-acetoneimine)]. These newly synthesized complexes have been characterized by elemental analysis, i.r. and electronic spectroscopy, molecular weight, electrolytic conductance and magnetic susceptibility measurements. Electronic spectra suggest that Co(tropolo ne)(baen) reacts with pyridine.     

Stability Constants of Cu(II) Hydroxypropylenediaminetetraacetates

Equilibrium of complexation between 2-hydroxypropylene-1,3-diamine-N,N,N,N-tetraethanoic acid (H₄L) and u²⁺ ions was studied by potentiometric and spectrophotometric methods. Stability constants of CuL^2– and CuHL^– complexes were determined at 298.15 K and I = 0.5 (KNO₃).     

The solid-state structure of (+)-(i)-menthyl 2-formamido-4, 4,4-trifluorobutanoate and the hydrogenation of the 2-butenoate precursor

Hydrogenation ofZ-(–)-(1R, 3R, 4S)-menthyl 2-formamido-4,4,4-trifluoro-2-butenoate catalyzed by Pd/C was performed at atmospheric pressure to yield a mixture of (2R, 1R, 3R, 4S)- and (2S, 1R, 3R, 4S)-menthyl 2-formamido-4,4,4-trifluorobutanoate diastereomers in a 5545 ratio, respectively. Repeated fractional crystallization from ethyl acetate and vapor diffusion of petroleum ether afforded (+)–(2S, 1R, 3R, 4S)-menthyl 2-formamido-4,4,4-trifluorobutanoate as clear colorless, crystalline prisms which were subjected to single-crystal X-ray diffraction analysis. The crystals belong to the orthorhombic system P2₁2₁2₁, and at 213 K:a=5.054(1),b= 10.000(2),c=32.707(1) Å,V=1652.9(4) ų,Z=4,R(F)=0.040, andR _w (F)=0.037. The finding of the (2S)-configuration for the formamido-acid portion of the (+)-ester enabled the configurational assignment of the asymmetric hydrogenation products ofZ-methyl 2-formamido-4, 4,4-trifluoro-2-butenoate catalyzed by chiral diphosphine/rhodium(I) complexes.     

Über Dihydro-bzw. Tetrahydrospiro([1]benzopyran-2,4′(1′H)-pyrimidin)-2′(3′H)-one

On reaction of dihydro-4,4,6-trimethyl-2(1H)-pyrimidinone1 with o-hydroxybenzaldehydes, dihydro- and tetrahydrospiro([1]-benzopyran-2,4(1H)-pyrimidin)-2(3H)-ones resp.5, 6, 7 are formed.     

Reaction of π-deficient aromatic heterocycles with ammonium polyhalides III. Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides

Summary Halogenation of phenothiazin-5-oxide with benzyltriethylammonium polyhalides (BTEA) under mild conditions afforded chloro- and bromophenothiazines as well as a few unexpected products e.g. 1,3,7,9-tetrachloro-phenothiazin-5-oxide, 7,3-dibromo-3, 10-diphenothiazinyl tribromide, and 7,3-dichloro-3,10-diphenothiazinyl tetrachloroiodate. A new charge-transfer complex of phenothiazine-5-oxide with bromine is reported.

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Reaktion elektronenarmer aromatischer Heterocyclen mit Ammoniumpolyhalogenverbindungen, 3. Mitt. Halogenierung von Phenothiazin-5-oxid mit Benzyltriethylammoniumpolyhalogeniden

Zusammenfassung Halogenierung von Phenothiazin-5-oxid mit Benzyltriethylammoniumhalogeniden (BTEA) unter milden Bedingungen ergab neben Chlor- und Bromphenothiazinen einige unerwartete Reaktionsprodukte wir z.B. 1,3,7,9-Tetrachlorphenothiazin-5-oxid, 7,3-Dibrom-3,10-diphenothiazinylbromid und 7,3-Dichlor-3,10-diphenothiazinyltetrachloriodat. Außerdem wird über einencharge-transfer-Komplex von Phenothiazin-5-oxid mit Brom berichtet.

     

Binuclear and mononuclear cobalt(II), nickel(II) and copper(II) complexes of 4,4′-bis(alkylaminoisonitrosoacetyl)diphenyl-methane derivatives

4,4-Bis(chloroacetyl)diphenylmethane has been prepared from ClCH₂COCl and Ph₂CH₂. 4,4-Methylenebis(phenylglyoxylohydroximoyl chloride has also been obtained. Four new substituted 4,4-bis(alkylaminoisonitrosoacetyl)diphenylmethanes (ligands) have been prepared from 4,4-methylenebis(phenylglyoxylohydroximoyl chloride) and the corresponding amines. The Ni^II, Cu^II and Co^II complexes of these ligands were prepared and their structures were identified using AAS, i.r., ¹H-n.m.r. spectral data, elemental analyses and magnetic susceptibility measurements.     

Nitration,amination, and halogenation of Di-O-methylphloracetophenone

Chlorination of the title compound gave 5- and 3-chloro-2-hydroxy-4,6-dimethoxyacetophenone. The nitration of its acetate, followed successively by reduction, diazotization, and reaction with cuprous chloride, gave the 3-substituted series, 2-acetoxy-4,6-dimethoxy-3-nitroacetophenone, 3-amino-2-hydroxy-4,6-dimethoxyacetophenone, and 3-chloro-2-hydroxy-4,6-methoxyacetophenone, respectively. The orientation of substituents in the products was proved. The amino and chloro members of the isomeric 5-substituted series were availablevia 2-hydroxy-4,6-dimethoxy-5-phenylazoacetophenone, the product of the reaction of the title compound with benzenediazonium chloride.

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Nitrierung, Aminierung und Halogenierung von Di-O-methylphloracetophenon

Zusammenfassung Chlorierung der Titelverbindung gab 5- und 3-Chlor-2-hydroxy-4,6-dimethoxyacetophenon. Die Nitrierung des Acetats, gefolgt von Reduktion, Diazotierung und Reaktion mit CuCl ergab die 3-substituierte Reihe: 2-Acetoxy-4,6-dimethoxy-3-nitroacetophenon, 3-Amino-2-hydroxy-4,6-dimethoxyacetophenon und 3-Chlor-2-hydroxy-4,6-dimethoxyacetophenon. Die Orientierung der Substituenten wird diskutiert. Die Amino- und Chlorderivate der isomeren 5-substituierten Reihe sind über 2-Hydroxy-4,6-dimethoxy-5-phenylacetophenon zugängig, dem Produkt der Reaktion der Titelverbindung mit Phenyldiazoniumchlorid.

     

Soluble polysaccharides of Rhodotorula flava

Conclusions 1. Xanthalin has been shown to have the structure of 2, 2-dimethyl-3, 4,-diangeloyloxy-3, 4-dihydropyrano-5, 6:6, 7-coumarin on the basis of the preparation of a number of derivatives and cleavage products.2. The following products of the alkaline hydrolysis of xanthalin have been isolated and characterized for the first time: (±)-3, 4-dihydroxy-3, 4-dihydroxanthyletin (isokhellactone), C₁₄H₁₄O₅, with mp 213–215° C and (–)-trans-3-hydroxy-4-methoxy-3, 4-dihydroxanthyletin (isomethylkhellactone, C₁₅H₁₆O₅, with mp 136.5–138° C and [] _D ²⁰ –47.7 (ethanol).Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 14–19, 1970