cas 7101-31-7, Dimethyldiselenide | Articles data

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Vibrational spectra and structure of dimethyl diselenide and dimethyl diselenide-d6
The vibrational behavior of the dimethyl diselenide and dimethyl diselenide-rfe molecules has been studied in the infrared region (4000-70 cm-1) and by Raman shifts (4000-50 cm-1). The molecule has been found to belong to point group C2. The fundamental vibrations, with the exception of the methyl torsions, have been assigned and supported by a normal-coordinate analysis.
Green, William H.,Harvey, Albert B.
p. 3586 - 3595
(1968)
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Aqueous phase preparation method of dialkyl diselenide ether compound
The method comprises the following steps: taking the compound represented by the formula (II) as a reaction raw material and I as a reaction raw material, and taking water or ethanol as a solvent under Se 40 - 75 °C conditions to obtain the reaction liquid to obtain the dialkyl diselenium ether compound shown in the formula (II KOH). The reaction is short in reaction time, does not need a metal catalyst, uses water as a solvent, and belongs to green and environment-friendly reaction. Economy, high efficiency, green, environmental protection.
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Paragraph 0032-0036

(2021/11/21)

Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes
A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.
Li, Sifeng,Yang, Qingjing,Bian, Zhaoxiang,Wang, Jun
supporting information
p. 2781 - 2785
(2020/03/30)

Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free
A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.
Lin, Xinxin,Fang, Zheng,Zeng, Cuilian,Zhu, Chenlong,Pang, Xinyan,Liu, Chengkou,He, Wei,Duan, Jindian,Qin, Ning,Guo, Kai
supporting information
p. 13738 - 13742
(2020/10/02)

Ultrasound-assisted synthesis of alkali metals diselenides (M2Se2) and their application for the gram-scale preparation of 2,2’-diselenobis(benzoic acid)
A simple and efficient method to convert elemental selenium into alkali metal diselenide was developed. The use of selenium and metal borohydride in a molar ratio of 1 to 0.125 in the presence of base, under “on water” conditions and ultrasound activation permitted the reduction of Se into Se22- to be completed within minutes. Thus obtained metal diselenide aqueous solution was then used in the multigram scale synthesis of 2,2’-diselenobis(benzoic acid) (DSBA) a valuable building block for the development of diverse and pivotal selenorganic compounds.
Krasowska, Dorota,Begini, Francesca,Santi, Claudio,Mangiavacchi, Francesca,Drabowicz, Jozef,Sancineto, Luca
p. 24 - 37
(2020/02/13)

Can dimedone be used to study selenoproteins? An investigation into the reactivity of dimedone toward oxidized forms of selenocysteine
Dimedone is a widely used reagent to assess the redox state of cysteine-containing proteins as it will alkylate sulfenic acid residues, but not sulfinic acid residues. While it has been reported that dimedone can label selenenic acid residues in selenoproteins, we investigated the stability, and reversibility of this label in a model peptide system. We also wondered whether dimedone could be used to detect seleninic acid residues. We used benzenesulfinic acid, benzeneseleninic acid, and model selenocysteine-containing peptides to investigate possible reactions with dimedone. These peptides were incubated with H2O2 in the presence of dimedone and then the reactions were followed by liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS). The native peptide, H-PTVTGCUG-OH (corresponding to the native amino acid sequence of the C-terminus of mammalian thioredoxin reductase), could not be alkylated by dimedone, but could be carboxymethylated with iodoacetic acid. However the “mutant peptide,” H-PTVTGAUG-OH, could be labeled with dimedone at low concentrations of H2O2, but the reaction was reversible by addition of thiol. Due to the reversible nature of this alkylation, we conclude that dimedone is not a good reagent for detecting selenenic acids in selenoproteins. At high concentrations of H2O2, selenium was eliminated from the peptide and a dimeric form of dimedone could be detected using LCMS and 1H NMR. The dimeric dimedone product forms as a result of a seleno-Pummerer reaction with Sec-seleninic acid. Overall our results show that the reaction of dimedone with oxidized cysteine residues is quite different from the same reaction with oxidized selenocysteine residues.
Payne, N. Connor,Barber, Drew R.,Ruggles, Erik L.,Hondal, Robert J.
p. 41 - 55
(2019/01/03)

Preparation method of high-purity selenomethionine
The invention discloses a preparation method of high-purity selenomethionine. The method comprises following steps: (1), synthesis of the dimethyl diselenide; (2), purification of dimethyl diselenide;(3), synthesis of crude selenomethionine sodium salt; and (4), purification of crude selenomethionine sodium salt. The yield of selenium in the selenomethionine prepared with the preparation method is larger than or equal to 80%, the selenomethionine content is larger than or equal to 99.5%, and the economic benefits are significant.
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Paragraph 0023-0026; 0030-0033; 0037-0040

(2019/09/17)

Simultaneous Construction of C?Se And C?S Bonds via the Visible-Light-Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2
A visible-light mediated multicomponent cascade reaction of diselenides, alkynes, and sulfur dioxide was developed, in which multiple C?Se and C?S bonds were constructed, and unexpected β-sulfonylvinylselane compounds were generated with high selectivity for E configuration. β-Sulfonylvinylselane transformation into 1,4-oxathiine-4,4-dioxide and sulfonylethyne derivates was then investigated. A plausible mechanism involving a selenium radical-initiated cascade reaction and sulfur dioxide insertion was proposed.
Chen, Hui,Ding, Rui,Tang, Haitao,Pan, Yingming,Xu, Yanli,Chen, Yanyan
supporting information
p. 3264 - 3268
(2019/09/17)

Structural variations on antitumour agents derived from bisacylimidoselenocarbamate. A proposal for structure-activity relationships based on the analysis of conformational behaviour
A molecular modelling study has been carried out on a previously reported series of symmetrically substituted bisacylimidoselenocarbamate (BSeC) derivatives that show remarkable antitumour activity in vitro against a panel of human tumour cell lines. These derivatives can be considered as a central scaffold constructed around a methyl carbamimidoselenoate nucleus in which two heteroarylacyl fragments are located on the scaffold nitrogen atoms, thus forming the different BSeCs. The results reveal that the nature of the selected heteroaryl ring has a marked influence on the antiproliferative activity of the compounds and this can be related, as a first approximation, to the ability to release methylselenol (MeSeH), a compound that, according to our initial hypothesis, is ultimately responsible for the antitumour activity of the compounds under investigation. The release of MeSeH from the active BSeCs has been confirmed by means of Head Space Gas Chromatography Mass Spectrometry techniques. The data that support this connection include the topography of the molecules, the conformational behaviour of the compounds, which influences the accessibility of the hydrolysis point, the interaction map obtained for an O2H type probe, and the location and energy of the HOMO/LUMO orbitals.
Font, María,Lizarraga, Elena,Ibá?ez, Elena,Plano, Daniel,Sanmartiń, Carmen,Palop, Juan A.
p. 489 - 498
(2013/10/01)

A convenient synthesis of D,L-selenomethionine
A convenient synthesis of D,L-selenomethionine from α-bromo-γ- butyrolactone in 4 steps and 26% overall yield has been described.
Ran,Cao,Wang,Lin
experimental part
p. 431 - 435
(2009/10/09)

Sterically encumbered hexakis(alkylseleno)benzenes: conformational behavior of hexakis(iso-propylselenomethyl)benzene toward Hg2+ ions on selective recognition
An efficient synthesis and structural aspects of a novel class of hexakis(alkylseleno)benzenes [(RSeCH2)6C6] (R = Me, iPr, nBu, sBu, tBu, nPn, nHx, nOct, 1-methylnaphthalene) by the reaction of hexakis(bromomethyl)benzene with RSe- ions is demonstrated. Preliminary data on ion-sensing properties reveal that these species may act as selective ionophores for Hg2+ ions.
Singh, Jai Deo,Maheshwari, Monika,Khan, Shabana,Butcher, Raymond J.
p. 117 - 121
(2008/04/13)

Reactions of 1,2-dihaloethanes with chalcogenide anions
Reactions of 1,2-dihaloethanes with chalcogenide anions generated from elemental chalcogens and dimethylchalcogens were performed in the hydrazine hydrate-KOH system. The use of anions Se x 2- and Te x 2- (x = 1-4) resulted in ethylene evolution and chalcogen regeneration (or in increased x value in an anion). Oligomers of Thiokol type formed only in the reaction of the 1,2-dichloroethane with a mixture of potassium disulfide and diselenide. The reductive cleavage of oligomers obtained in the hydrazine hydrate-KOH system followed by methylation led to the formation of 1,2-bis(methylthio)ethane, 1-methylseleno-2- methylthioethane, and 1,2-bis(methylseleno)ethane. The features of substitution with chalcogenide anions in vicinal dihalides are discussed. Mass spectra of compounds obtained were measured and analyzed. Pleiades Publishing, Inc. 2006.
Russavskaya,Grabel'nykh,Levanova,Sukhomazova,Klyba,Zhanchipova,Tatarinova,Elaev,Deryagina,Korchevin,Trofimov
p. 652 - 658
(2007/10/03)

Condition-driven selective syntheses of dialkyl diselenides involving elemental selenium and sodium borohydride
Dialkyl diselenides have been prepared from alkyl halides, sodium borohydride and elemental selenium using two different methods. One of them involves the intermediate formation of diselenide dianion equivalent ( -SeSe-).
Krief, Alain,Derock, Michel
p. 1012 - 1014
(2007/10/03)

Convenient route to dialkyl diselenides from alkyl tosylates. Synthesis of di(cis-myrtanyl) diselenide
A one-step method for the synthesis of dialkyl diselenides, by reaction of alkyl tosylates with sodium diselenide is described. Three variants of the synthesis, using as an example the preparation of optically active di(cis-myrtanyl) diselenide, are compared.
?cianowski, Jacek
p. 3331 - 3334
(2007/10/03)

Stabilization of sulfenyl(poly)selenide ions in N,N-dimethylacetamide
Whereas redox processes resulted from the reactions PhSe-/S8 or PhSe2Ph/S3·-, mixed anions RSSey- (R = Ph, PhCH2; y = 1-3) were obtained by the slow addition of solid selenium to thiolate ions in N,N-dimethylacetamide. The RS- + n Se reactions, which were investigated by spectroelectrochemistry, led initially (n = 1) only to the formation of RSSe- ions. These species oxidized into RS2R faster than RS- on a gold electrode, with the simultaneous electrodeposition of very reactive microcrystals of selenium. On a preparative scale, the substitution of RSSe- ions (R = CH3, Ph) on alkyl halides yielded RSSeR′ compounds (R′ = PhCH2, CH3, respectively) which greatly disproportionated. Further additions of Se (n = 2, 3) to RS- ions led to RSSe2- and RSSe3- in equilibrium with RS2R and mixtures of Sex2- polyselenide ions (x = 4,6; 6,8). Visible spectra of RSSe2- and RSSe3- ions were calculated from the study of the backward reactions RS2R + Sex2- (x = 4, 6).
Ahrika, Abdelkader,Robert, Julie,Anouti, Meriem,Paris, Jacky
p. 1433 - 1439
(2007/10/03)

Synthesis of diselenides and selenides from elemental selenium
Sodium hydride is able to reduce elemental selenium to sodium diselenide (Na2Se2), but not to sodium selenide (Na2Se). Dialkyl diselenides and even dialkyl selenides, including unsymmetrical dialkyl selenides, can be nevertheless synthesized using the proper Se/NaH ratio (1/1 or 1/2).
Krief, Alain,Derock, Michel
p. 3083 - 3086
(2007/10/03)

NEW ROUTE TO ORGANIC SELENIDES AND TELLURIDES
A new simple and convenient synthetic route to organic chalcogenides R2Y (R = alkyl, allyl, benzyl; Y = Se, Te) is developed, which involves generation of Se2- and Te2- anions from Se and Te in the system KOH-hydrazine hydrate, where the latter plays the role of both the medium and reducing agent.Subsequent alkylation of the anions with the corresponding alkyl halides furnishes the target chalcogenides in almost 95percent yield.Alkyl chlorides react faster than alkyl bromides and alkyl iodides.
Korchevin, N. A.,Podkuiko, P. A.,Stankevich, V. K.,Deryagina, E. N.,Trofimov, B. A.
p. 85 - 87
(2007/10/03)

Convenient Syntheses of N,N-Dialkylselenoamides and N,N,N',N'-Tetraalkylselenoureas by Treating Terminal gem-Dihaloalkanes, Chloroform , or Sodium Trichloroacetate with a Base, Elemental Selenium, and Amines
Treatment of terminal gem-dihaloalkanes, chloroform or sodium trichloroacetate with elemental selenium in the presence of NaH and an excess amount of primary or secondary amines gave selenoamides and selenoureas in modest yields.
Takikawa, Yuji,Yamaguchi, Minoru,Sasaki, Tohru,Ohnishi, Kenji,Shimada, Kazuaki
p. 2105 - 2108
(2007/10/02)

Synthesis and Stereochemistry of Optically Active Selenonium Imides
Diastereomeric mixtures of 4-phenyl(methyl)selenonium-N-toluene-4'-sulfonimides (dia.-1) amd 4-phenyl(2',4',6'-triisopropylphenyl)selenonium-N-toluene-4''-sulfonimides (dia.-7) were synthesized.Optical resolution by the fractional recrystallization of dia.-7 from methanol gave the optically pure (-)-selenonium imide as stable crystals.The absolute configuration around the selenium atom was determined to be S based on the CD spectra.The kinetics for the epimerization by pyramidal inversion of the optically active selenonium imide were studied.
Kamigata, Nobumasa,Taka, Hideo,Matsuhisa, Ayumi,Matsuyama, Haruo,Shimizu, Toshio
p. 2257 - 2264
(2007/10/02)

A NEW REACTION OF DIALLYL SELENIDE, LEADING TO 1,3,5-HEXATRIENE
In the highly basic potassium hydroxide-DMSO system at 50-80 deg C diallyl selenide is converted into 1,3,5-hexatriene.Alkyl allyl selenides do not enter into this reaction but undergo isomerization to alkyl 1-propenyl selenides.
Musorin, G. K.,Amosova, S. V.
p. 519 - 522
(2007/10/02)

Synthesis and Stereochemistry of an Optically Selenonium Ylide. X-Ray Molecular Structure of (+)Se-phenyl>(methyl)selenonium 4,4-Dimethyl-2,6-dioxocyclohexylide
Fractional recrystallization of diastereoisomeric phenyl>(methyl)selenonium 4,4-dimethyl-2,6-dioxocyclohexylide from hexane-diethyl ether gave the optically pure (+)-selenonium ylide as stable crystals.The absoute configuration around the selenium atom was determined to be R by X-ray crystallographic analysis.The epimerization of the optically active selenonium ylide by pyramidal inversion was studied.
Kamigata, Nobumasa,Nakamura, Yoshihiro,Kikuchi, Koichi,Ikemoto, Isao,Shimizu, Toshio,Matsuyama, Haruo
p. 1721 - 1728
(2007/10/02)

The First Synthesis of Se-Methyl Carboxylic Thionoselenolesters
Reaction of carboxylic thionoesters with dimethylaluminium methylselenolate in diethyl ether gave the corresponding Se-methyl thionoselenolesters in 87-98percent yield.
Khalid, Mohamed,Ripoll, Jean-Louis,Vallee, Yannick
p. 964 - 965
(2007/10/02)

(1)H and (13)C NMR Studies on the Positional Isomers of Methyl Selenalaurate and Telluralaurate
A report is given of the (1)H and (13)C NMR spectra of a series of methyl selenalaurates and telluralaurates in which successive methylene groups have been replaced by a selenium or a tellurium atom.The effect on contiguous carbons is a marked upfield shift (shielding) while the protons attached to these carbons are deshielded.The β-and γ protons are weakly deshielded.
Lie Ken Jie, Marcel S. F.,Yan-Kit, Cheung,Chau, Sherman H.,Yan, Bonnie F. Y.
p. 501 - 508
(2007/10/02)

Efficient, high yield oxidation of thiols and selenols to disulphides and diselenides
Thiols and selenols are smoothly oxidised in high yield to disulphides and diselenides by sodium perborate at room temperature.
McKillop,Koyuncu,Krief,Dumont,Renier,Trabelsi
p. 5007 - 5010
(2007/10/02)

PREPARATIVE METHODS FOR THE SYNTHESIS OF DIALKYL DISELENIDES
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Korchevin, N. A.,Podkuiko, P. A.,Stankevich, V. K.,Deryagina, E. N.,Voronkov, M. G.
p. 1592 - 1594
(2007/10/02)

Efficient Syntheses of Diselenides from Selenols
Diselenides are quite instantaneously and quantitatively prepared by oxidation of selenols with 30 percent aqueous hydrogen peroxide or with the corresponding seleninic acids.
Krief, A.,Mahieu, A. F. De,Dumont, W.,Trabelsi, M.
p. 131 - 133
(2007/10/02)

LITHIUM ORGANYL-POLYCHALCOGENOLATES
Lithium organyl-selenolates, RSeLi or tellurolates, RTeLi insert further equivalents of chalcogens with formation of selenyl-selenolates, RSeSeLi or tellurenyl-tellurolates, RTeTeLi (R=Me, n-Bu, s-Bu, t-Bu, Ph).Mixed anions are only formed if the chalcogen insertion order corresponds with an increase of electronegativity, i.e.: RTeSeLi, RTeSLi, RSeSLi and n-BuTeSeSLi.All species have been characterized by 77-Se and 125-Te NMR-spectroscopy.Tellurenyl-tellurolates and tellurenyl-selenolates are stable at room temperature, selenyl-selenolates and chalcogenyl-thiolatesdisproportionate.The chemical integrity of the chalcogenyl-chalcogenolates was checked by methylation with methyl triflate.The formed organyl-methyl-dichalcogenides exhibit symmetrization equilibria that are also obtained by mixing the symmetric conpounds.Oxidation of tellurenyl-selenolates affords di(organyl-tellurenyl) selenides, (RTe)2Se (R=Me, n-Bu, t-Bu, Ph, p-MeC6H4, 2-thienyl) and (RTe)2Se2 for R=(Me3Si)3C.In solution (RTe)2Se are in equilibrium with R2Te2 and (RTe)2Se2.
Koellemann, Christoph,Obendorf, Dagmar,Sladky, Fritz
p. 69 - 78
(2007/10/02)

Preparation and Characterization of Alkane- and Arene-Chalcogenolate Complexes of η5-Cyclopentadienyltitanium(IV): First Synthesis of 5-C5H5)(SeCH3)3>
A simple synthesis of (1) (cp=η5-C5H5) from and BBr3 is described.Reaction of complex (1) with Na(SCH3) or Li(SeR) (R=CH3 or C6H5) afforded the derivatives (2), (3), or (4), respectively.Complexes (2)-(4) were characterized by (1)H n.m.r., i.r. and mass spectroscopy; (3) the first example of a cyclopentadienyltris(selenolato)titanium compound, was also studied by (77)Se n.m.r. spectroscopy.The oxidation and hydrolysis behaviour of (2) and (3) in solution is discussed on the basis of their (1)H n.m.r. spectra.
Klapoetke, Thomas,Koepf, Hartmut,Gowik, Petra
p. 1529 - 1532
(2007/10/02)

CONCISE SYNTHESES OF L-SELENOMETHIONINE AND OF L-SELENOCYSTINE USING RADICAL CHAIN REACTIONS
L-Selenomethionine and L-selenocystine were prepared in high overall yields from protected L-glutamic and L-aspartic acid derivatives respectively.Irradiation of the mixed anhydrides (esters) derived from 4 (e.g. 15) in the presence of dimethyldiselenide provided the protected L-selenomethionine 16 directly.We have shown that triselenocyanide Se3(CN)2 can serve as an efficient selenocyanating agent for radicals; the selenocyanide group is a good precursor for the diselenide moiety of L-selenocystine.
Barton, Derek H. R.,Bridon, Dominique,Herve, Yolande,Potier, Pierre,Thierry, Josiane,Zard, Samir Z.
p. 4983 - 4990
(2007/10/02)

SYNTHESIS OF SELENOACETALS
This paper reports our results concerning the syntheses of various bis(alkylseleno)alkanes and some of their arylseleno analogues by different methods.The scope and limitation of each of them are presented.
Clarembeau, M.,Cravador, A.,Dumont, W.,Hevesi, L,Krief, A.,et al.
p. 4793 - 4812
(2007/10/02)

The Convenient Syntheses of Organoselenium Reagents
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Syper, Ludwig,Mlochowski, Jacek
p. 439 - 442
(2007/10/02)

Gas Phase Reactions, 23. Thermal decomposition of Open-Chain Dialkyl Sulfides, Disulfides and Diselenides
The thermal decomposition of the dialkyl chalcogenide derivatives RSR, RSSR and RSeSeR (R = CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, C(CH3)3) in a heated flow tube is analyzed and optimized using PE spectroscopy.Whereas high-temperature pyrolysis >1000 K yields mixtures of thermodynamically favored final products like H2, CH4, CS2, and HCCH, the lowest thermal reaction channel produces homogeneously olefin, H2S, and sulfur or olefin, alkaneselenol, H2Se, and selenium, respectively.The decomposition temperatures increase from RSeSeR via RSSR towards RSR and also with decreasing size of the alkyl groups.Based on the experimental data the possible course of the thermal decomposition is discussed.
Hirabayashi, Takakuni,Mohmand, Shamsher,Bock, Hans
p. 483 - 491
(2007/10/02)

REACTIONS OF TRIADS S8-KOH-DMSO, Se8-KOH-DMSO, Te-KOH-HMPA WITH ACETYLENES
A new general approach to anionic transformations of acetylenes using superbasic media has been developed.It allows series of new reactions which are not undergone by acetylene under conventional conditions.The triads S8-KOH-dimethylsulfoxide (DMSO), Se8-KOH-DMSO, Te-KOH-hexamethyl-phosphorictriamide (HMPA) are proposed as new effective reagents for the preparation of unsaturated compounds of sulfur, selenium and tellurium.A series of reactions of acetylene with sulfur, selenium and tellurium proceeding in DMSO or HMPA in the presence of alkali and water at 80-120 deg C leading to divinyl sulfide, divinyl selenide and divinyl telluride in 25-80percent yields have been found.Thiophen, di-1-(1,3-butadienyl) sulfide, 1-vinyl-2-thiabicyclohept-3-ene, and dihydrothiophen have been obtained by the reaction of vinylacetylene with sulfur.The reaction of vinylacetylene with selenium affords selenophen, di-1-(1,3-butadienyl) selenide, 1-vinyl-2-selenabicyclohept-3-ene, methyl (1-(1,3-butadienyl) sulfide, and methylthiomethyl 1-(1,3-butadienyl) selenide, vinyl 1-(1,3-butadienyl) sulfide and methylthiomethyl 1-(1,3-butadienyl) selenide (the latter two with DMSO participation).The reaction of vinylacetylene with tellurium gives mainly di-1-(1,3-butadienyl) telluride.A series of reactions between DMSO and selenium leading to dimethyl sulfide, dimethyl sulfoselenide, and methylthiomethyl selenide have been observed.
Trofimov, B. A.,Amosova, S. V.,Gusarova, N. K.,Musorin, G. K.
p. 713 - 718
(2007/10/02)

Reduction vs. Acetalisation of some Carbonyl Compounds by means of Methylselenol and Lewis Acids
Aliphatic ketones and aromatic carbonyl compounds on reaction with methylselenol and a Lewis acid, are shown to undergo acetalisation and/or reduction to methyl selenide, the unexpected reduction reaction being predominant in most cases.
Cravador, Alfredo,Krief, Alain,Hevesi, Laszlo
p. 451
(2007/10/02)