Relevant bibliographies by topics / Grignard reagents. Organomagnesium compounds

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Academic literature on the topic 'Grignard reagents. Organomagnesium compounds'

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Published: 4 June 2021
Last updated: 10 February 2022

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Journal articles on the topic "Grignard reagents. Organomagnesium compounds"

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Berton, Mateo, Kevin Sheehan, Andrea Adamo, and D. Tyler McQuade. "Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides." Beilstein Journal of Organic Chemistry 16 (June 19, 2020): 1343–56. http://dx.doi.org/10.3762/bjoc.16.115.

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Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.
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Matsubara, Hiroshi, Yuki Niwa, and Ryosuke Matake. "A Grignard-Type Phase-Vanishing Method: Generation of Organomagnesium Reagent and Its Subsequent Addition to Carbonyl Compounds." Synlett 26, no. 09 (March 30, 2015): 1276–80. http://dx.doi.org/10.1055/s-0034-1380381.

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Matsubara, Hiroshi, Yuki Niwa, and Ryosuke Matake. "ChemInform Abstract: A Grignard-Type Phase-Vanishing Method: Generation of Organomagnesium Reagent and Its Subsequent Addition to Carbonyl Compounds." ChemInform 46, no. 39 (September 2015): no. http://dx.doi.org/10.1002/chin.201539047.

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Clark, Peter D., Russell S. Mann, and Kevin L. Lesage. "Reactions of dimethyl polysulfides with organomagnesium reagents." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 29–33. http://dx.doi.org/10.1139/v92-006.

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Reactions of a mixture of dimethyl polysulfides (DMPS, CH3SxCH3, x = 3 – 8) with methyl- and phenylmagnesium halides are described. The type of product obtained was dependent on the molar ratio of DMPS to Grignard reagent. When a 6:1 methyl-Grignard to DMPS ratio was used, methanethiol and dimethyl sulfide were the major products obtained after acidification of the reaction mixture. Lesser quantities of methyl-Grignard favored the formation of dimethyl sulfide, dimethyl disulfide, and H2S. Experiments with a 6:1 phenylmagnesium bromide to DMPS ratio produced benzenethiol and phenylmethyl sulfide as major products after acidification. No methanethiol was observed in these experiments. Mixtures of phenylmethyl mono-, di-, and trisulfides and H2S were obtained with a 3:1 Grignard/DMPS molar ratio. From a mechanistic viewpoint, product distributions obtained from reaction of Grignard reagents with DMPS can be explained by the formation of magnesium thiolates that are most readily stabilized by adjacent structures. Experiments using phenyl Grignard reagent in limited supply suggested that the internal sulfur atoms of the polysulfide chains were most reactive. Keywords: organic polysulfides, Grignard reagents.
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Dzhemilev, U. M., A. G. Ibragimov, and G. A. Tolstikov. "Synthesis and transformations of “non-grignard” organomagnesium reagents obtained from 1,3-dienes." Journal of Organometallic Chemistry 406, no. 1-2 (March 1991): 1–47. http://dx.doi.org/10.1016/0022-328x(91)83169-5.

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Inoue, Atsushi, Junichi Kondo, Hiroshi Shinokubo, and Koichiro Oshima. "Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds." Chemistry - A European Journal 8, no. 7 (April 2, 2002): 1730–40. http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6.

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Gilman, Henry, Edith L. St. John, Nina B. St. John, and Myrl Lichtenwalter. "Relative reactivities of organometallic compounds. XI Grignard reagents." Recueil des Travaux Chimiques des Pays-Bas 55, no. 7 (September 3, 2010): 577–85. http://dx.doi.org/10.1002/recl.19360550708.

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Knochel, Paul, Matthias A. Schade, Sebastian Bernhardt, Georg Manolikakes, Albrecht Metzger, Fabian M. Piller, Christoph J. Rohbogner, and Marc Mosrin. "Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents." Beilstein Journal of Organic Chemistry 7 (September 13, 2011): 1261–77. http://dx.doi.org/10.3762/bjoc.7.147.

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In this review we summarize the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein. Experimental details are given for the most important reactions in the Supporting Information File 1 of this article.
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Fujdala, Kyle L., David W. K. Gracey, Erica F. Wong, and Kim M. Baines. "The addition of organometallic reagents to tetramesityldigermene." Canadian Journal of Chemistry 80, no. 11 (November 1, 2002): 1387–92. http://dx.doi.org/10.1139/v02-128.

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The thermolysis and photolysis of hexamesitylcyclotrigermane in the presence of ethylmagnesium bromide has been investigated. Under photochemical conditions, ethyldimesitylgermane, 1,2-diethyl-1,1,2-trimesityldigermane and ethyl-1,1,2,2-tetramesityldigermane were isolated and, under thermal conditions, 1,2,2-triethyl-1,1-dimesityl digermane and 2,2-diethyl-1,1,1-trimesityldigermane were isolated. The photolysis of hexamesitylcyclotrigermane in the presence of methyllithium has also been investigated. In both cases, the organometallic reagent adds to tetramesityl digermene and dimesitylgermylene formed by photochemical or thermal cleavage of the cyclotrigermane. In the case of the addition of the Grignard reagent, the resulting germyl Grignard reagent undergoes a facile ligand exchange reaction.Key words: digermene, germylene, Grignard reagents, alkyllithium reagents, germylmagnesium compounds, germyllithium compounds.
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Alberti, Angelo, Massimo Benaglia, Dante Macciantelli, Massimo Marcaccio, Antonio Olmeda, Gian Franco Pedulli, and Sergio Roffia. "Reactions between Grignard Reagents and Thiocarbonyl Compounds: A Revisitation." Journal of Organic Chemistry 62, no. 18 (September 1997): 6309–15. http://dx.doi.org/10.1021/jo9708001.

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Dissertations / Theses on the topic "Grignard reagents. Organomagnesium compounds"

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Mandai, Kyoko. "Cu-Catalyzed Enantioselective Allylic Substitutions with Organomagnesium and Organoaluminum Reagents Promoted by N-Heterocyclic Carbenes for the Formation of Quaternary Stereogenic Centers." Thesis, Boston College, 2010. http://hdl.handle.net/2345/1329.

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Thesis advisor: Amir H. Hoveyda
Chapter One: An overview of Cu-catalyzed enantioselective allylic substitutions with organometallic reagents. Chapter Two: Development of Cu-catalyzed enantioselective allylic alkylations of allylic chlorides with Grignard reagents for the formation of all-carbon quaternary stereogenic centers is disclosed. Chapter Three: Development of Cu-catalyzed enantioselective allylic substitutions of allylic phosphates with alkyl, aryl, and heterocyclic aluminum reagents for the formation of quaternary stereogenic centers is discussed
Thesis (MS) — Boston College, 2010
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Naeemi, Qaseem [Verfasser]. "Studies in Enantioselective Transition Metal Catalysis Using Modular Phosphine-Phosphite Ligands Copper-catalyzed 1,4-Addition of Grignard Reagents to alpha,beta-Unsaturated Carbonyl Compounds / Qaseem Naeemi." München : Verlag Dr. Hut, 2012. http://d-nb.info/1020299428/34.

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Milton, Edward J. "Pd catalysed C-C & C-O bond formation using bis-(dialkyl/diarylphosphino)ferrocene ligands." Thesis, University of St Andrews, 2010. http://hdl.handle.net/10023/1022.

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A brief introduction explaining phosphine ligand properties, Pd catalysed cross-coupling reactions; the importance of the steps involved in the catalytic cycle (oxidative addition, transmetalation & reductive elimination), mechanistic studies and a comparison of various reactions will give an overview of important cross-coupling reactions and their limitations. The development of a “super-concentrated” (5M) Pd catalysed Kumada type coupling reaction has been developed for coupling a range of aryl bromide and chloride substrates with the Grignard reagents ((p-CF₃-C₆H₄)MgBr)) and PhMgBr in methyl-tetrahydrofuran (Me-THF). Using a range of bidentate ligands such as bis-phosphinoferrocenyl ligands, good conversions were achieved using small amounts of solvent; up to 10 times less than typical procedures in THF. The unsymmetrical Pt complexes of the form [Pt(P-P)Br₂], [Pt(P-P)(Ph)Br] and [Pt(P-P)Ph₂] have been synthesised and characterised. The variations of substituents on the ligand system and the steric bulk have been shown to have a dramatic effect on the rate of transmetalation. The results provide one explanation why 1,1’-bis(di tert-butylphosphino)ferrocene (dtbpf), an excellent ligand for certain Suzuki reactions, is quite poor in reactions where transmetalation is more difficult. Palladium dichloride complexes of the ferrocenylphosphine based ligands 1,1’-bis- (diphenylphosphino)ferrocene (dppf), 1,1’-bis-(diisopropylphosphino)ferrocene (dippf) and 1,1’-bis-(di-tert-butylphosphino)ferrocene (dtbpf) have been shown to be active in the Hiyama cross-coupling of p-bromoacetophenone and vinyltrimethoxysilane (CHCH₂Si(OMe₃)) in the presence of TBAF under thermal heating and microwave conditions. Ligands with the optimum balance for promoting the transmetalation, oxidative addition and reductive elimination steps along the reaction pathway have been identified. Competition experiments are consistent with slow transmetalation being an issue with the Hiyama reaction relative to the Suzuki coupling. A novel protocol has been developed for the synthesis of aryl-alkyl ethers via C-O bond activation under Pd catalysed conditions. Utilising the unsymmetrical 1-bis-(ditertbutyl-1’- bis-diphenylphosphino)ferrocene (dtbdppf) under optimised conditions with silicon based nucleophiles and NaOH or TBAF as an activator, the formation of methyl, ethyl, n-propyl and n-butyl ethers with a range of aryl halides was achieved in good yield.
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Chen, Chiar-Dy, and 陳嘉迪. "1.The Substitution Reactions of Organomagnesium Copper Reagents and S,S-Dimethyldithiocarbonate 2. Magnesium Bromide Promoted Intramolecular Cyclization Reactions of Grignard Reagents and Acetals." Thesis, 1997. http://ndltd.ncl.edu.tw/handle/36377329455353330595.

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碩士
國立臺灣大學
化學系
85
This thesis contains twe parts: In the first part we discuss the substitution reactions of organomagnesium copper reagents, which were prepaired from Grignard reagents, and the loaner of phosgene, S,S-dimethtldithiocarbonate (DMDTC). We can obtain the disubsti- tuted ketones, even monosubstituted thioesters as products. In the second parts we found that magnesium bromide promoted intramolecular cyclization reactions of Grignard reagents and acetals. By using this method, we can easily get the products which contain 3, 4 or 5 memberd rings.
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Cheng, Wen-Lung, and 鄭文龍. "Reactions of Grignard Reagents with Compounds Containing Carbon- Sulfur and Carbon-Oxygen Bonds." Thesis, 1993. http://ndltd.ncl.edu.tw/handle/25997437876046270175.

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"Metallation of 8-methylquinoline." Chinese University of Hong Kong, 1993. http://library.cuhk.edu.hk/record=b5887206.

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by Lawrence Tin-chi Law.
Thesis (M.Phil.)--Chinese University of Hong Kong, 1993.
Includes bibliographical references (leaves 96).
acknowledgements --- p.iii
ABSTRACT --- p.iv
CONTENTS --- p.v
ABBREVIATION --- p.vii
Chapter CHAPTER I --- METALLATION OF 8-METHYLQUINOLINE
Chapter 1.1 --- INTRODUCTION --- p.1
Chapter 1.1.1 --- A Brief Review of Metal-Alkyl Chemistry --- p.1
Chapter 1.1.2 --- General Considerations --- p.2
Chapter 1.1.3 --- 8-Methylquinoline as Ligand Precursor --- p.8
Chapter 1.1.4 --- Metallations by Organolithium Compounds --- p.9
Chapter 1.1.5 --- Other Methods for Metallations --- p.16
Chapter 1.1.6 --- Aim of the Present Work --- p.21
Chapter 1.2 --- RESULTS AND DISCUSSION --- p.24
Chapter 1.2.1 --- Reactions of 8-Methylquinoline with Organolithium Reagents --- p.26
Chapter 1.2.2 --- Synthesis of Grignard Reagent --- p.35
Chapter 1.2.3 --- Attempted Metal-Halogen Exchange Reaction at Low Temperature --- p.39
Chapter 1.2.4 --- Metallation of 8-methylquinoline by Lithium Diisopropylamide --- p.40
Chapter 1.3 --- EXPERIMENTAL FOR CHAPTER I --- p.43
Chapter 1.4 --- REFERENCES FOR CHAPTER I --- p.53
Chapter CHAPTER II --- SYNTHESIS AND CHARACTERISATION AND STRUCTURE OF SOME MAIN GROUP 14 ALKYLS
Chapter 2.1 --- INTRODUCTION --- p.58
Chapter 2.1.1 --- General Aspects of Group 14 Organometallic Compounds --- p.58
Chapter 2.1.2 --- Group 14 Organometallic Confounds --- p.59
Chapter 2.1.3 --- Subvalent Group 14 Metal Alkyls --- p.63
Chapter 2.2 --- RESULTS AND DISCUSSION --- p.67
Chapter 2.2.1 --- Synthesis of Five Co-ordinated Tin (IV) Compound --- p.67
Chapter 2.2.2 --- Molecular Structure of [Sn{8-(CHSiMe3)C9H6N}Ph2Cl] --- p.70
Chapter 2.2.3 --- Synthesis of Group 14 Subvalent Metal Complexes --- p.74
Chapter 2.3 --- EXPERIMENTAL FOR CHAPTER II --- p.76
Chapter 2.4 --- REFERENCES FOR CHAPTER II --- p.79
Chapter CHAPTER III --- SYNTHESIS AND CHARACTERISATION OF SOME GROUP 12 (ZINC AND CADMIUM) METAL DIALKYLS
Chapter 3.1 --- INTRODUCTION --- p.81
Chapter 3.1.1 --- A General Aspect of Group 12 Organometallics --- p.81
Chapter 3.2 --- RESULTS AND DISCUSSION --- p.88
Chapter 3.2.1 --- Synthesis of Group 12 Organometallic Confounds --- p.88
Chapter 3.2.2 --- Molecular Structure of [Cd{8-(CHSiMe3)C9H6N}(tmeda)Cl] --- p.91
Chapter 3.3 --- EXPERIMENTAL FOR CHAPTER III --- p.93
Chapter 3.4 --- REFERENCES FOR CHAPTER III
APPENDIX I
Chapter 1. --- GENERAL PROCEDURES --- p.97
Chapter 2. --- PHYSICAL AND ANALYTICAL MEASUREMENTS --- p.100
APPENDIX II
LIST OF SELECTED 1H NMR SPECTRA --- p.101
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Books on the topic "Grignard reagents. Organomagnesium compounds"

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Sanchez, Ramiro. The chemistry of unsolvated organomagnesium compounds. 1985.

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Book chapters on the topic "Grignard reagents. Organomagnesium compounds"

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Westerhausen, Matthias, Jens Langer, Sven Krieck, Reinald Fischer, Helmar Görls, and Mathias Köhler. "Heavier Group 2 Grignard Reagents of the Type Aryl-Ae(L) n -X (Post-Grignard Reagents)." In Alkaline-Earth Metal Compounds, 29–72. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-36270-5_2.

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Rösch, L. "From Sn(II) Compounds with Organomagnesium-Halide Reagents." In Inorganic Reactions and Methods, 328–29. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470145241.ch194.

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Ortiz, Pablo, Francesco Lanza, and Syuzanna R. Harutyunyan. "1,2- Versus 1,4-Asymmetric Addition of Grignard Reagents to Carbonyl Compounds." In Progress in Enantioselective Cu(I)-catalyzed Formation of Stereogenic Centers, 99–134. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/3418_2015_164.

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Clark, J. H. "From Alkaline-Earth Metals with Carbon-Halogen Compounds (Formation of Organomagnesium Reagents)." In Inorganic Reactions and Methods, 76–78. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470145180.ch44.

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"Organomagnesium Compounds as Polymerization Initiators." In Handbook of Grignard Reagents, 713–30. CRC Press, 1996. http://dx.doi.org/10.1201/b16932-37.

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Scerri, Eric. "More Chemistry." In The Periodic Table. Oxford University Press, 2019. http://dx.doi.org/10.1093/oso/9780190914363.003.0019.

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The trends within rows and columns of the periodic table are quite well known and are not repeated here. Instead, I concentrate on a number of other chemical trends, some of which challenge the form of reductionism that attempts to provide explanations based on electronic configurations alone. In the case of one particular trend described here, the knight’s move, the chemical behavior defies any theoretical understanding whatsoever, at least at the present time. As is well known to students of inorganic chemistry, a small number of elements display what is termed diagonal behavior where, in apparent violation of group trends, two elements from adjacent groups show greater similarity than is observed between these elements and the members of their own respective groups. Of these three classic examples of diagonal behavior, let us concentrate on the first one to the left in the periodic table, that between lithium and magnesium. The similarities between these two elements are as follows:1. Whereas the alkali metals form peroxides and superoxides, lithium behaves like a typical alkaline earth in forming only a normal oxide with formula Li2O. 2.Unlike the other alkali metals, lithium forms a nitride, Li3N, as do the alkaline earths. 3.Although the salts of most alkali metals are soluble, the carbonate, sulfate, and fluorides of lithium are insoluble, as in the case of the alkaline earth elements. 4.Lithium and magnesium both form organometallic compounds that act as useful reagents in organic chemistry. Lithium typically forms such compounds as Li(CH3)3, while magnesium forms such compounds as CH3MgBr, a typical Grignard reagent that is used in nucleophilic addition reactions. Organolithium and organomagnesium compounds are very strong bases that react with water to form alkanes. 5.Lithium salts display considerable covalent character, unlike their alkali metal homologues but in common with many alkaline earth salts. 6.Whereas the carbonates of the alkali metals do not decompose on heating, that of lithium behaves like the carbonates of the alkaline earths in forming the oxide and carbon dioxide gas. 7.Lithium is a considerably harder metal than other alkali metals and similar in hardness to the alkaline earths.
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Singaram, Bakthan. "With Grignard Reagents." In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00476.

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Pornet, J. "Via Grignard Reagents." In Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-004-00724.

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Keay, B. A. "Via Grignard Reagents." In Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-004-00744.

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Gennari, C., S. Ceccarelli, and U. Piarulli. "From Vinylic Grignard Reagents." In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00309.

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