A Convenient Preparation of Trimethylborane and Triethylborane

Köster, Roland; Binger, Paul; Dahlhoff, W. V.

doi:10.1080/00945717308057281

Cited by 81 publications

(11 citation statements)

References 8 publications

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“…The best promotor was a mixed anhydride of a carboxylic acid and a dialkylboric acid R2B0C0R t . We also found that the diethylborylation of hydroxy groups could be achieved with, the easily obtainable, triethylborane (5) in the presence of small amounts of diethylborylpTvalate Et2B0C0tBu. The following two equations illustrate the proposed catalytic cycle of the O-diethylborylation.…”

Section: Koster and Dahloff Ethylboron Compoundsmentioning

confidence: 79%

Applications of Ethylboron Compounds in Carbohydrate Chemistry

Köster

Dahlhoff

1977

ACS Symposium Series

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The fundamental work of Böeseken (1) in the first half of this century showed that the element boron has different affinities towards the various polyhydroxy compounds. The early investigations demonstrated the stereospecifity of the various polyols and saccharides towards boric acid. One analytical application that developed from this work was the quantitative determination of boron based on the interaction of boric acid with certain hydroxy compounds. However, it is the preparative aspects that are of interest to carbohydrate chemists, and we will present here some of the uses of organoboron compounds in synthetic work and show the advantages they offer over conventional blocking groups.The most important and well known application of organoboron compounds in sugar chemistry was, and is still, the use of the bifunctional O-phenylboranediyl--ligand as a protective group. Some O-phenylboranediyl derivatives of monosaccharides have been described in the literature (2,3). They have been prepared from phenylboric acid, which is neither as easy to react nor as easy to remove as the O-ethylboron group. The products are often not volatile and cannot be purified by distillation. Usually crystallisation is used to purify the products, but this is often difficult to achieve.In the past three years we have discovered new methods for the preparation of boron derivatives of hydroxy compounds and in particular O-ethylboron compounds. We were thus able to apply our 20 years of experience in the field of organoboranes to carbohydrate chemistry. The combination of two separate fields of research often brings about new impetus to the development of science. We believe that by combining our expertese in the field of sugars and 1

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Section: Koster and Dahloff Ethylboron Compoundsmentioning

confidence: 79%

Applications of Ethylboron Compounds in Carbohydrate Chemistry

Köster

Dahlhoff

1977

ACS Symposium Series

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“…Route II (Dulcitol and BEts in the Ratio 1:4). Dulcitol (20 g, 110 mmol) was added in portions over 4 h to triethylborane (43 g, 439 mmol) containing 0.2 ml of diethylboryl pivalate. The temperature rose to a maximum of 50 °C and ethane (9.59 nl, 97.5%, MS) was liberated.…”

Section: Methodsmentioning

confidence: 99%

“…Proof of the structure of 3 is furnished by its facile selective deborylation to 4 (see Scheme II), which involves opening of the nine-membered ethylboranediyl ring.…”

mentioning

confidence: 99%

Boron compounds. 40. O-Ethylboranediyl derivatives of dulcitol

Dahlhoff¹,

Koêster²

1976

J. Org. Chem.

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“…Alle Arbeiten wurden unter strengem Ausschluß von Feuchtigkeit und Sauerstoff durchgeführt. Die Ausgangsverbindungen 2 [10], 4 [11] und 5 [12] …”

Section: Experimentellesunclassified

2,5-Dihydro-1,2,5-azoniastannaboratole: Nützliche Vorstufen für die Heterocyclensynthese / 2,5-Dihydro-1,2,5-azoniastannaboratole: Useful Steps for the Synthesis of Heterocycles

Kerschl¹,

Wrackmeyer²

1985

Zeitschrift Für Naturforschung B

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Abstract Organoboration, Heterocycles, Multinuclear NMR 1,1-Organoboration of diethylamino-dimethyl-(1-propynyl)stannane (6), formed by an exchange reaction between the bis(propynyl)-(4) and bis-(diethylamino)dimethylstannane (5), with trimethyl-(2a) or triethylborane (2b) leads to highly reactive new heterocyclic compounds (7). Both, the coordinative N→B and the weak Sn-N bond are readily attacked by H-acidic compounds. Ammonia or primary amines are used as examples. Multinuclear NMR (1H, 11B, 13C, 15 N, 119Sn) data serve for the characterization.

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A Convenient Preparation of Trimethylborane and Triethylborane

Cited by 81 publications

References 8 publications

Applications of Ethylboron Compounds in Carbohydrate Chemistry

Applications of Ethylboron Compounds in Carbohydrate Chemistry

Boron compounds. 40. O-Ethylboranediyl derivatives of dulcitol

2,5-Dihydro-1,2,5-azoniastannaboratole: Nützliche Vorstufen für die Heterocyclensynthese / 2,5-Dihydro-1,2,5-azoniastannaboratole: Useful Steps for the Synthesis of Heterocycles

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