- 2,2'-Bi[benzo[b]thiophene]: An unexpected isolation of the benzo[b]thiophene dimer
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The crystal structure of 2,2'-bi[benzo[b]thiophene], C16H 10S2, at 173K has triclinic (P1) symmetry. It is of interest with respect to its apparent mode of synthesis, as it is a by-product of a Stille cross-coupling reaction in which it was not explictly detected by spectroscopic methods. It was upon crystal structure analysis of a specimen isolated from the mother liquor that this reaction was determined to give rise to the title compound, which is a dimer arising from the starting material. Two independent half-molecules of this dimer comprise the asymmetric unit, and the full molecules are generated via inversion centers. Both molecules in the unit cell exhibit ring disorder, and they are essentially identical because of their rigidity and planarity.
- Cheung, Eugene Y.,Pennington, Lewis D.,Bartberger, Michael D.,Staples, Richard J.
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- Advantage of arch-shaped structure on transistor performances over linear-shaped structure in dibenzothienopyrrole semiconductors
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To understand the influence of molecular shape on the optoelectronic properties of heteroacenes, we report here the syntheses and characterizations of two linear- and two arch-shaped dibenzothienopyrrole (DBTP) derivatives, namely, N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole (l-HDBTP), N-phenyldibenzothieno[3,2-b:2′,3′-d]pyrrole (l-PDBTP), N-hexyldibenzothieno[2,3-b:3′,2′-d]pyrrole (a-HDBTP) and N-phenyldibenzothieno[2,3-b:3′,2′-d]pyrrole (a-PDBTP). Their structure-property relationships have been systematically studied by optical absorption, cyclic voltammetry, single-crystal X-ray diffraction analyses and the single-crystal-based and thin-film-based field-effect transistors (FETs). The results demonstrate that the arch-shaped DBTP derivatives can modify their electronic structures and molecular arrangements by tuning of substituents, to obtain a better charge-transporting ability relative to the linear-shaped ones. The arch-shaped N-phenyl substituted a-PDBTP exhibits optimum molecular π-stacking arrangement and charge transport properties, with the hole mobility of 0.75 cm2V?1s?1 and 0.058 cm2V?1s?1 for the single-crystal and the thin-film OFETs, respectively. These results indicate that the arch-shaped DBTP core is a promising building block in the area of organic semiconducting materials.
- Mu, Wenjing,Sun, Su,Zhang, Jing,Jiao, Mingyang,Wang, Wentao,Liu, Yanwei,Sun, Xiangnan,Jiang, Lang,Chen, Bozhen,Qi, Ting
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- Oxidative Homocoupling of Diheteroaryl- or Diarylmanganese Reagents Generated via Directed Manganation Using TMP2Mn
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We report an oxidative homocoupling of diheteroaryl or diarylmanganese reagents prepared by directed manganation using TMP2Mn·2MgCl2·4LiCl. The resulting diorganomanganese reagents can efficiently undergo an oxidative dimerization leading to the homocoupling products in good yields. Remarkably, a number of functional groups, as well as sensitive heterocycles are tolerated using this metalation-dimerization procedure.
- Haas, Diana,Hammann, Jeffrey M.,Moyeux, Alban,Cahiez, Gérard,Knochel, Paul
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- Synthesis and properties of the anti and syn isomers of dibenzothieno[b,d]pyrrole
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A novel type of anti and syn isomers of a pentacyclic compound consisting of two thiophene rings and one pyrrole ring were efficiently synthesized from benzo[b]thiophene, and the anti isomer exhibits better charge transport and OFET properties compared with the syn isomer and its N-hexyl substitution. The Royal Society of Chemistry.
- Qi, Ting,Guo, Yunlong,Liu, Yunqi,Xi, Hongxia,Zhang, Hengjun,Gao, Xike,Liu, Ying,Lu, Kun,Du, Chunyan,Yu, Giu,Zhu, Daoben
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- Stereoselective synthesis of monoamine reuptake inhibitor NS9544 acetate
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(-)-3-(2-Benzothienyl)-8-H-8-azabicyclo[3,2,1]oct-2-ene acetate, NS9544 acetate, is a candidate drug intended to treat pain and other CNS disorders. In the synthetic route tropinone was enantioselective deprotonated with a chiral lithium amide derived from [R-(R*,R*)]-bis(α-methylbenzyl) amine hydrochloride. The formed enolate was trapped as triflate and coupled with benzo[b]thiophene-2-boronic acid under Suzuki conditions. To further enhance the enantiomeric purity crystallisation with l-(+)-tartaric acid was performed. Finally N-demethylation with trichloroethylchloroformate followed by treatment with acetic acid afforded NS9544 as the acetate salt with high enantiomeric purity.
- Malmgren, Hakan,Cotton, Hanna,Frostrup, Brian,Jones, David Spencer,Loke, Marie-Louise,Peters, Dan,Schultz, Sara,Soelver, Ellen,Thomsen, Tove,Wennerberg, Johan
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- Divergent Carbocatalytic Routes in Oxidative Coupling of Benzofused Heteroaryl Dimers: A Mechanistic Update
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Mildly thermal air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2’-dimers, e.g., 2-(benzofuran-2-yl)-1H-indole, to chiral 3,3’-coupled cyclooctatetraenes or carbazole-type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl-type arenium cation mechanisms lead to different products with 2-(benzofuran-2-yl)-1H-indole, being in accord with experimental product distributions.
- Casadio, David S.,Aikonen, Santeri,Lenarda, Anna,Nieger, Martin,Hu, Tao,Taubert, Stefan,Sundholm, Dage,Muuronen, Mikko,Wirtanen, Tom,Helaja, Juho
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supporting information
p. 5283 - 5291
(2021/02/26)
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- Iron-catalysed regioselective thienyl C–H/C–H coupling
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Regioselective thienyl–thienyl coupling is arguably one of the most important transformations for organic electronic materials. A prototype of ideal organic synthesis to couple two thienyl groups by cutting two C–H bonds requires formal removal of two hydrogen atoms with an oxidant, which often limits the synthetic efficiency and versatility for oxidation-sensitive substrates (for example, donor and hole-transporting materials). Here, we found that diethyl oxalate, used together with AlMe3, acts as a two-electron acceptor in an iron-catalysed C–H activation. We describe the regioselective thienyl C–H/C–H coupling with an iron(III) catalyst, a trisphosphine ligand, AlMe3 and diethyl oxalate under mild conditions. The efficient catalytic system accelerated by ligand optimization polymerizes thiophene-containing monomers into homo- and copolymers bearing a variety of electron-donative π motifs. The findings suggest the versatility of iron catalysis for the synthesis of functional polymers, for which the potential of this ubiquitous metal has so far not been fully appreciated. [Figure not available: see fulltext.].
- Doba, Takahiro,Ilies, Laurean,Nakamura, Eiichi,Sato, Wataru,Shang, Rui
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p. 631 - 638
(2021/07/25)
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- Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst
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Substituted bithiophenes are prominent fragments in functional organic materials, and they are ideally prepared via direct oxidative C-H/C-H coupling. Here, we report a novel PdII catalyst system, employing 1,10-phenanthroline-5,6-dione (phd) as the ancillary ligand, that enables aerobic oxidative homocoupling of 2-bromothiophenes and other related heterocycles. These observations represent the first use of phd to support Pd-catalyzed aerobic oxidation. The reaction also benefits from a Cu(OAc)2 cocatalyst, and mechanistic studies show that Cu promotes C-C coupling, implicating a role for CuII different from its conventional contribution to reoxidation of the Pd catalyst.
- Tereniak, Stephen J.,Bruns, David L.,Stahl, Shannon S.
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supporting information
p. 20318 - 20323
(2020/12/01)
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- Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes
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A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.
- Canivet, Jér?me,Grousset, Léonie,Hisler, Ga?lle,Mohr, Yorck,Quadrelli, Elsje Alessandra,Roux, Yoann,Wisser, Florian M.
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supporting information
p. 3155 - 3161
(2020/06/19)
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- Copper- and Cobalt-Catalyzed Syntheses of Thiophene-Based Tertiary Amines
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Thienylzinc halides and related compounds prepared by deprotonation followed by transmetalation were used in copper-catalyzed amination using N-benzoyloxy secondary amines. By extending the reaction to 1,5-naphthyridine, it was showed that the competitive dimer formation observed in the case of thiophenes was linked with the low stability of some thienylamines rather than homocoupling. Interestingly, thienylzinc halides and related compounds prepared by transmetalation of thienylmagnesium halides, either prepared from their bromo-precursors or generated by deprotometalation, were satisfactorily employed in cobalt-catalyzed aminations. Finally, aminothiophenes were involved in copper-catalyzed mono- and di-N-arylations, affording differently substituted di- and triphenylamines.
- Bouarfa, Salima,Gra?l, Simon,Ivanova, Maria,Langlais, Timothy,Bentabed-Ababsa, Ghenia,Lassagne, Frédéric,Erb, William,Roisnel, Thierry,Dorcet, Vincent,Knochel, Paul,Mongin, Florence
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p. 3244 - 3258
(2019/06/08)
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- Method for Aerobic Oxidative Coupling of Thiophenes with a Ligand-Supported Palladium Catalyst
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An oxidative homocoupling method of synthesizing certain 2,2′-bithiophenes from thiophenes using oxygen as the terminal oxidant is disclosed. In non-limiting examples, the method uses oxygen along with a catalytic system that includes palladium, an assistive ligand, and a non-palladium metal additive to catalyze one of the following reactions: Associated catalytic systems and compositions are also disclosed.
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Paragraph 0095; 0108; 0122-0124
(2019/07/23)
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- Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation
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A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.
- Pei, Xiaocong,Zhou, Guan,Li, Xuejing,Xu, Yuchen,Panicker, Resmi C.,Srinivasan, Rajavel
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supporting information
p. 5703 - 5707
(2019/06/19)
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- Palladium-catalyzed homo-coupling of heteroarylsulfoniums via borylation/Suzuki-Miyaura coupling sequence
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Palladium-catalyzed homo-coupling of heteroaryldimethylsulfoniums proceeds in the presence of bis(pinacolato)diboron and a base to yield biheteroaryls. The homo-coupling involves palladium-catalyzed borylation and the subsequent Suzuki-Miyaura coupling. As the sulfoniums were able to be prepared in situ from the corresponding heteroaryl sulfides and methyl triflate, one-pot transformations of heteroaryl sulfides into the homo-coupling products were executed. Furthermore, a facile synthesis of a highly substituted 2,2'-bibenzofuran was accomplished with a combination of Pummerer-type synthesis of 2-benzofuryl sulfide and the present homo-coupling.
- Minami, Hiroko,Nogi, Keisuke,Yorimitsu, Hideki
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p. 998 - 1007
(2019/04/26)
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- Efficient Homocoupling of Aryl- and Alkenylboronic Acids in the Presence of Low Loadings of [{Pd(μ-OH)Cl(IPr)} 2 ]
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NHC-palladium(II) complex [{Pd(μ-OH)Cl(IPr)} 2 ] (IPr = bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) catalyzes the oxidative coupling of a broad spectrum of aryl- and alkenylboronic acids at loadings down to 5 ppm. At the concentration of 0.05 mol% the catalyst permits an efficient reaction under base-free conditions.
- Ostrowska, Sylwia,Rogalski, Szymon,Lorkowski, Jan,Walkowiak, Jedrzej,Pietraszuk, Cezary
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supporting information
p. 1735 - 1740
(2018/07/21)
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- BENZOTHIOPHENE DERIVATIVES AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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The present invention relates to a compound represented by following general formula (I): wherein R1 and R2 are independently selected from a substituted or unsubstituted C4 to C30 arylamine group, a substituted or unsubstituted C4 to C40 carbazole group, a substituted or unsubstituted C4 to C40 benzothiophene group or a substituted or unsubstituted C4 to C40 benzofuran group; L is a bridging group, and selected from a single bond substituted C4 to C40 arylamine group, a substituted C4 to C40 carbazole group, a substituted C4 to C40 benzothiophene group, O atom, N atom or S atom; R3-R10 are independently selected from H atom, a C1-C20 aliphatic compound containing linear or branched alkanes, alkenes or alkynes or a C6-C30 aromatic group, or two adjacent groups linking to be a ring forming a naphthothiophene derivatives; m and n are selected from integers of 1 to 3, as well as the addition of m and n is larger than 0 but less than or equal to 3. Also, the present invention relates to organic electroluminescent devices using the compound represented by general formula (I), especially a hole transporting material, a hole injecting material or a main material of organic luminescent material used in an OLED device.
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Paragraph 0511; 0512; 0513
(2017/10/28)
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- BENZOTHIOPHENE DERIVATIVE AND USE THEREOF IN ORGANIC ELECTROLUMINESCENT FIELD
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The present invention refers to type (I) as relates to compounds to be represented by, state and used in the R 1 and R 2 in an independently a substituted or unsubstituted C 4-C 30amine it will be biting of, a substituted or unsubstituted C 4-C 40 for dozing, , a substituted or unsubstituted C 4-C 40 of benzo mote five pen or a substituted or unsubstituted C 4-C 40 of benzo [...] and, selected from a, L is the bridging group, single joined, C 4-C 40 of substituted arylamine, C 4-C 40 carbazole-substituted, C 4-C 40 substituted benzothiophene, oxygen atoms, nitrogen atoms or sulfur and one selected from nuclear reactor, R 3-R 10 independently H atoms, C 1-C 20 aliphatic straight or branched chain hydrocarbon groups or C 6-C 888000081488 8 selected from aromatic group or two groups is connected adjacent the upper end the ring form a derivatives [...] , m, integer of at 0-3 graphical object is selected from the n, 3 the m+n less than or equal is greater than 0. The present invention refers to in addition said types of compound use in organic electroluminescence device protects the material exhibits hole-transporting by performing a polishing process in particular OLED, hole injection material or organic light-emitting material protection a main composition.
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Paragraph 0440-0444
(2016/10/09)
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- Ligand-, base-, co-catalyst-free copper fluorapatite (CuFAP) as a versatile, ecofriendly, heterogeneous and reusable catalyst for an efficient homocoupling of arylboronic acid at ambient reaction conditions
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This paper describes the first report in which copper species containing copper fluorapatite (CuFAP) acts as a versatile, eco-friendly, recyclable, heterogeneous catalyst for an efficient synthesis of symmetric biaryls from the homo-coupling of arylboronic acids in methanol solvent at ambient reaction conditions. The developed protocol is ligand-, base-, and co-catalyst-free, sustainable, mild, inexpensive, and compatible with a wide range of aromatic/heterocyclic boronic acids and provides the corresponding products in excellent yields without purification. The catalyst was easily recovered from the reaction mixture and reused several times without loss of activity.
- Mulla, Shafeek A. R.,Chavan, Santosh S.,Pathan, Mohsinkhan Y.,Inamdar, Suleman M.,Shaikh, Taufeekaslam M. Y.
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p. 24675 - 24680
(2015/03/30)
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- Clay encapsulated Cu(OH)x promoted homocoupling of arylboronic acids: An efficient and eco-friendly protocol
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Cu(OH)x has been encapsulated over montmorillonite-KSF by simple ologomeric deposition strategy. The resulting catalyst has been employed for selective homocoupling of arylboronic acids under ambient conditions without requirement of any ligand or base. This catalyst is easy to recover and shows excellent reusability without losing its activity. Techniques like XRD, SEM, TPR, IR, BET surface area measurement and XPS were used to characterize the catalyst. The present method promises for the simple and clean homocoupling of arylboronic acids.
- Dar, Bashir Ahmad,Singh, Snehil,Pandey, Nalini,Singh,Sharma, Priti,Lazar, Anish,Sharma, Meena,Vishwakarma, Ram A.,Singh, Baldev
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p. 232 - 238
(2014/01/06)
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- Rhodium-catalyzed intermolecular oxidative cross-coupling of (hetero)arenes with chalcogenophenes
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A straightforward and efficient method for the rhodium-catalyzed intermolecular oxidative cross-coupling of arenes and heteroarenes with thio- and selenophene derivatives (chalcogenophenes) via double C-H bond cleavage has been developed by using Cu(OAc)2/AgSbF6 as an oxidant. The reaction is applicable to a wide range of (hetero)arenes carrying a directing group and chalcogenophenes to yield substituted biaryl heterocyclic derivatives and oligothiophene derivatives in moderate to high yields.
- Reddy, Vutukuri Prakash,Qiu, Renhua,Iwasaki, Takanori,Kambe, Nobuaki
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supporting information
p. 1290 - 1293
(2013/04/24)
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- Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization
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"Chemical Equation Presented" A number of first-row transition metal salts catalyze deprotonative dimerization of acidic arenes. Under the atmosphere of oxygen, nickel, manganese, cobalt, and iron chlorides have been shown to dimerize five- and six-membered ring heterocycles as well as electron-poor arenes. Both tetramethylpiperidide and dicyclohexylamide bases can be employed; however, the former afford slightly higher yields.
- Truong, Thanh,Alvarado, Joseph,Tran, Ly Dieu,Daugulis, Olafs
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supporting information; experimental part
p. 1200 - 1203
(2010/06/13)
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- Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species
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In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.
- Snegaroff, Katia,L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Nguyen, Tan Tai,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
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experimental part
p. 10280 - 10290
(2010/04/24)
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- Synthesis and mixed lineage kinase activity of pyrrolocarbazole and isoindolone analogs of (+)K-252a
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Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B and F are important to MLK activity. Heteroatom and alkyl replacement of the N-12 and/or N-13 indole nitrogen atoms identified the nonplanar dihydronaphthyl[3,4-a] pyrrolo[3,4-c]carbazole-7-one (8) and corresponding 5,7-dione (7) as potent cell-permeable MLK1/3 family-selective leads with in vitro activity comparable to that of (+)K-252a and determined them to be 2- to 3-fold more potent than the aglycone natural product K-252c.
- Hudkins, Robert L.,Johnson, Neil W.,Angeles, Thelma S.,Gessner, George W.,Mallamo, John P.
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p. 433 - 441
(2007/10/03)
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- Palladium-Catalyzed C-H Homocoupling of Thiophenes: Facile Construction of Bithiophene Structure
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Palladium-catalyzed C-H homocoupling of thiophene derivatives takes place in the presence of silver(I) fluoride or acetate. A variety of bithiophenes are obtained in good to excellent yields. In particular, the reaction of 2-bromothiophene proceeds at room temperature to afford 5,5′-dibromo-2,2′-bithiophene, where the bromine atom is completely intact in the palladium-catalyzed reaction. XRD analysis reveals that silver fluoride is reduced to silver(0) during the reaction. Copyright
- Masui, Kentaro,Ikegami, Haruka,Mori, Atsunori
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p. 5074 - 5075
(2007/10/03)
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- Oxidative dimerization: Pd(II) catalysis in the presence of oxygen using aqueous media
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Reported herein is a method for the formation of symmetric biaryls and dienes via oxidative dimerization of aryl and alkenyl boronic acids. These conditions utilized Pd(II) catalysts under an oxygen atmosphere with water as the solvent. The use of phase transfer catalysts promoted efficient and mild syntheses of a wide range of materials.
- Parrish, Jay P.,Jung, Young C.,Floyd, Ryan J.,Jung, Kyung Woon
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p. 7899 - 7902
(2007/10/03)
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- A Convenient Synthetic Route to bis-Heteroaromatic and bis-Heterocyclic Compounds Promoted by Liganded Nickel Complex Reducing Agents.
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A number of nitrogen, sulfur or oxygen containing bis-heteroaromatic or bis-heterocyclic derivatives have been synthesized in good to excellent yields by homocoupling of the corresponding halogenated compounds in the presence of liganded (triphenylphosphine or 2,2'-bipyridine) nickel Complex Reducing Agents in THF or DME at 63 deg C.
- Forst, Yves,Becker, Sandrine,Caubere, Paul
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p. 11893 - 11902
(2007/10/02)
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- Addition Reactions of Benzothiophen. Part 1. Self-addition and Addition of Simple Aromatic Hydrocarbons
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Benzothiophen undergoes facile addition reactions across the 2,3-bond when treated with aluminium chloride in an appropriate solvent at 0 or 20 deg C.In carbon disulphide or dichloromethane, it undergoes self-addition to give two or more of the four possible 2- or 3-(2- or 3-benzothienyl)2,3-dihydrobenzothiophens (3)-(6).In the presence of an aromatic solvent, the dimerization reaction just mentioned predominates at low temperatures (0 deg C or below), or at room temperature if the solvent is benzene, chlorobenzene, t-butylbenzene, isopropylbenzene, or 1,3,5-trimethylbenzene.At room temperature, in toluene, ethylbenzene, and 1,2- or 1,4-dimethylbenzene, solvent addition occurs to give a mixture of the corresponding 2- and 3-aryl-2,3-dihydrobenzenethiophens.At 80 deg C, benzene and toluene give the fully aromatic 2-arylbenzothiophen.The reactions are discussed in terms of an ionic mechanism involving protonation of benzothiophen by moist aluminium chloride and reaction of the resulting electrophile with benzothiophen or with an aromatic substrate.
- Clark, Peter David,Clarke, Kenneth,Ewing, David F.,Scrowston, Richard M.
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p. 677 - 685
(2007/10/02)
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