Die Synthese des Cantharidins

Ziegler, K.; Schenck, Günther O.; Krockow, E. W.; Siebert, A.; Wenz, Adolf; Weber, Hedda K.

doi:10.1002/jlac.19425510102

Cited by 58 publications

(24 citation statements)

References 29 publications

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“…of the starting material and the amount of NBS between 1.25-2.5 eq. of the starting material [6,7]. When we tested the bromination reaction of 1 using AIBN catalyst between 0.01 and 0.30 eq.…”

Section: Resultsmentioning

confidence: 99%

“…The benzyl radical bromination reactions have been carried out using some corrosive bromine sources such as elemental bromine [2][3][4] or N-bromoimides [5]. Nowadays a method using a relatively safe and user-friendly brominating agent, N-bromosuccinimide (NBS) is established as the typical procedure, i.e., NBS in refluxing CCl4 in the presence of a radical initiator such as benzoyl peroxide or 2, 2′-azobis(isobutyronitrile) known as the Wohl-Ziegler bromination [6,7]. However, this protocol suffers from the use of the toxic and ozone-depleting solvent CCl4 [8], due to its ozone-depleting capability, this solvent has been internationally banned (Montreal Protocol), and its use is therefore prohibited on an industrial scale [9].…”

Section: Introductionmentioning

confidence: 99%

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Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester

Lee¹,

Sup²

2016

Clean Technology

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The benzylic bromination of methoxyimino-o-tolyl-acetic acid methyl ester (1) into (2-bromomethyl-phenyl)-methoxyiminoacetic acid methyl ester (2) using N-bromosuccinimide in the presence of 2,2'-azobisisobutyronitrile in various reaction solvents were investigated. The efficiency of the reaction was found to be sensitive to the kind of reaction solvents. We found the benzylic bromination of 1 to 2 can be performed in 1,2-dichlorobenzene as reaction solvent superior to the classic Wohl-Ziegler procedure in both reaction time and isolated yield (8 h vs 12 h, 92 vs 79%). This system provides clean, rapid, and high-yielding reactions with replacement of conventional solvents, such as tetrachloromethane, by less-toxic 1,2-dichlorobenzene.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester

Lee¹,

Sup²

2016

Clean Technology

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“… Free‐radical chemistry (for example, the preparation of the 1,1,3,3‐tetraphenylallyl radical and pentaphenylcyclopentadienyl radical)9 Organolithium reagents (for example, preparation of n ‐butyllithium)10 Carbometalation as in the addition of 2‐phenylisopropylpotassium to stilbene11 Polymerization of butadiene using alkali‐metal carbanions as initiators12 N ‐bromosuccinimide‐mediated allylic and benzylic bromination13 Synthesis of cantharidin and other natural products14 …”

Section: The Karl Ziegler Eramentioning

confidence: 99%

One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung

Reetz

2014

Angew Chem Int Ed

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This Essay is an account of the institutional and scientific development of the Max‐Planck‐Institut für Kohlenforschung in Mülheim an der Ruhr (Germany), which is the successor to the Kaiser‐Wilhelm‐Institut für Kohlenforschung founded in 1914. The Essay is divided into four main parts, corresponding to the four major periods which are closely associated with the respective Directors of the Institute from 1914 to 2014: 1) Franz Fischer; 2) Karl Ziegler; 3) Günther Wilke; and 4) the period beginning with Manfred T. Reetz, who established a directorate comprising five Directors of equal status, each heading a different research department under the banner of catalysis. Along with key historical events associated with the Institute, research highlights of the four periods are featured.

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“…B. Herstellung von n ‐Butyllithium)10 Carbometallierung, z. B. bei der Addition von 2‐Phenylisopropylkalium an Stilben11 Polymerisation von Butadien durch Alkalimetallagentien als Initiatoren12 N ‐Bromsuccinimid‐vermittelte allylische and benzylische Bromierung13 Synthese von Cantharidin und anderen Naturstoffen14…”

Section: Die Karl‐ziegler‐äraunclassified

100 Jahre Max‐Planck‐Institut für Kohlenforschung

Reetz

2014

Angewandte Chemie

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Dieser Essay beschreibt die institutionelle und wissenschaftliche Entwicklung des Max‐Planck‐Instituts für Kohlenforschung in Mülheim an der Ruhr, des Nachfolge‐Instituts des 1914 gegründeten Kaiser‐Wilhelm‐Instituts für Kohlenforschung. Die vier Hauptteile des Essays entsprechen den vier historischen Perioden, die mit den jeweiligen Direktoren zusammenhängen: 1) Franz Fischer; 2) Karl Ziegler; 3) Günther Wilke; 4) die von Manfred T. Reetz initiierte Umstrukturierung, in deren Folge ein Direktorium bestehend aus fünf gleichberechtigten Direktoren mit jeweils einer Abteilung etabliert wurde. Zusätzlich zu den rein historischen und politischen Entwicklungen werden auch Höhepunkte der Forschung aus den vier Perioden beschrieben.

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Die Synthese des Cantharidins

Cited by 58 publications

References 29 publications

Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester

Benzylic Brominations with N-Bromosuccinimide in 1,2-Dichlorobenzene: Effective Preparation of (2-Bromomethyl-phenyl)-Methoxyiminoacetic Acid Methyl Ester

One Hundred Years of the Max‐Planck‐Institut für Kohlenforschung

100 Jahre Max‐Planck‐Institut für Kohlenforschung

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