The Cleavage of Ethers with Boron Bromide. I. Some Common Ethers

Benton, F. L.; Dillon, T. E.

doi:10.1021/ja01257a035

Cited by 116 publications

(63 citation statements)

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“…HMW DOM samples (8-10 mg C in 10 -15 ml) were also analyzed for the presence of ether bound lipids with boron tribromide (BBr3, Aldrich) (90°C for 4h) according to Benton and Dillon (1942). All reactions were performed in sealed tubes under nitrogen.…”

Section: Lipid Analysismentioning

confidence: 99%

High molecular weight (HMW) dissolved organic matter (DOM) in seawater : chemical structure, sources and cycling

Aluwihare¹

1999

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Section: Lipid Analysismentioning

confidence: 99%

High molecular weight (HMW) dissolved organic matter (DOM) in seawater : chemical structure, sources and cycling

Aluwihare¹

1999

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“…Um aus den M ethoxygruppen in den Verbindungen 7 -9 die freien Hydroxygruppen zu erhalten, m üs sen die Ether gespalten werden. Die gängigste M e thode hierzu ist die Verwendung von Bortribrom id in absolutem Methylenchlorid bei -7 8 °C [14,15] [16,17]. Die Liganden 10 und 11 sind bei pH 6 wasserlöslich und werden bei Raum tem peratur mit einer äquimolaren wäßrigen Lösung von K 2PtC l4 versetzt.…”

Section: Synthese Der Liganden Und Komplexeunclassified

Synthese und Antitumoraktivität von [1,2-Diamino-1-(p-hydroxy)benzyl]ethan(dichloro)platin(II)-Komplexen<br />Synthesis and Antitumor Activity of [1,2-Diamino-1-(p-hydroxy)benzyl]ethane(dichloro)platinum(II) Complexes

Brunner

Maiterth

Treittinger

1992

Zeitschrift Für Naturforschung B

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The complexes [l,2-diam ino-l-(/?-hydroxy)benzyl-l-(methyl, ethyl, and phenyl)]ethane-(dichloro)platinum(II) were synthesized and characterized. The benzylic ^-hydroxy group of the 1,2-diaminoethane ligand leads to good water-solubility o f the complexes. The ligands were synthesized in a Strecker-type reaction, starting from the corresponding /?-methoxybenzylketones. The amino nitriles were reduced to the diamines. Finally, the /?-methoxy groups were converted into hydroxy groups by ether cleavage. For the preparation of the complexes, K 2PtCl4 was added to the ligands. The antitum or activity o f the platinum(II) compounds was tested towards the hum an m am m ary carcinoma cell line M DA-M B 231. The antitum or effect depends on the substituents and increases in the series phenyl, methyl, and ethyl. As a maxi mum, a growth inhibition value of 77% was obtained.

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“…dt 3.93 (2H) J= 140+ 6 Hz, m 6.8 (3H), m 7,15 (2H). [7][8][9][10][11][12][13] CJbutan (8) 1.1 g 7 wurden analog zur Darstellung von 6 in " o o> ... das Tosylat überführt und dieses ohne weitere Reinigung zu einer Lösung aus 0,7 g LiBr und 10 ml absol. Aceton gegeben und 2 h unter Rückfluß erhitzt [7].…”

Section: -Phenoxy[4-13 C]-1-butanolunclassified

“…Ether gelöst und bei -45 °C unter N2-Atmosphäre mit 17 ml DIBAH-Lösung (0.98 M/n-Hexan) versetzt [8], Nach Rühren bei Raumtemperatur (24 h [ 1.5-13 Co]-pentan (11) 1,0 g 10 wurde in 10 ml Petrolether gelöst und unter Eiskühlung und No-Atmosphäre mit 0.3 ml BBr3 versetzt [9]. Nach 2 h Kochen unter Rückfluß wurde mit Pentan verdünnt und mit Eis/Wasser hvdrolysiert, die org.…”

Section: -Brom-1 -Phenoxy-unclassified

Eliminierung von Aceton und Bildung von protoniertem Aceton bei der chemischen Ionisation von [2.2.6.6]-Tetramethylcyclohexanon/ Elimination of Acetone and Formation of Protonated Acetone from [2,2,6,6]-Tetramethylcyclohexanone under the Condition of Chemical Ionisation

Wolfschütz

Franke

Heinrich

et al. 1982

Zeitschrift Für Naturforschung B

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Abstract By means of appropriately D and 13C labelled precursors it is shown that the proton catalysed degradation of [2,2,6,6]-tetramethyl cyclohexanone {e.g. elimination of acetone and formation of protonatecl acetone from [MH]+) proceeds via two distinct pathways. The energetically favoured one (pathway A, Scheme 1) involves a sequence of [1,2]-methyl migration, ring contraction and methyl migration, whereas the energetically less attractive path B commences with a Wagner-Meerwein ring contraction, followed by hydroxyl and methyl migration. Semi-empirical quantum mechanical calculations (MNDO) are em-ployed to explore computationally relevant parts of the potential energy surface. The syntheses of the specifically 13C labelled title compounds (1 a, b) are described in detail.

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The Cleavage of Ethers with Boron Bromide. I. Some Common Ethers

Cited by 116 publications

References 0 publications

High molecular weight (HMW) dissolved organic matter (DOM) in seawater : chemical structure, sources and cycling

High molecular weight (HMW) dissolved organic matter (DOM) in seawater : chemical structure, sources and cycling

Synthese und Antitumoraktivität von [1,2-Diamino-1-(p-hydroxy)benzyl]ethan(dichloro)platin(II)-Komplexen<br />Synthesis and Antitumor Activity of [1,2-Diamino-1-(p-hydroxy)benzyl]ethane(dichloro)platinum(II) Complexes

Eliminierung von Aceton und Bildung von protoniertem Aceton bei der chemischen Ionisation von [2.2.6.6]-Tetramethylcyclohexanon/ Elimination of Acetone and Formation of Protonated Acetone from [2,2,6,6]-Tetramethylcyclohexanone under the Condition of Chemical Ionisation

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