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Reactions of dialkylbromoboranes with alkali metal hydrides in the presence of alkenes. Synthesis of ‘mixed’ trialkylboranes (RA2RBB) in solution

Maddocks, Peter J., Pelter, Andrew, Rowe, Keith, Smith, Keith and Subrahmanyam, Chitti 1981. Reactions of dialkylbromoboranes with alkali metal hydrides in the presence of alkenes. Synthesis of ‘mixed’ trialkylboranes (RA2RBB) in solution. Journal of the Chemical Society, Perkin Transactions 1 (2) , pp. 653-656. 10.1039/P19810000653

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Abstract

Dialkylbromoboranes react steadily with hydroxide-free sodium hydride in diglyme, in the presence of alkenes, to give nearly quantitative yields of partly mixed trialkylboranes. The reaction proceeds too slowly to allow prior clean preparation of dialkylboranes, so reaction in the presence of alkenes possessing hydride-sensitive functional groups is not possible, although terminal alkynes can be hydroborated in situ by a modified experimental procedure. Potassium hydride reacts much more rapidly with dialkylbromoboranes, the reactions being complete within minutes at 20 °C, but the yields are lower. Addition of dibenzo-18-crown-6 leads to an increase in yield but the results are still inferior to those obtained using sodium hydride. Reaction of dialkylbromoboranes with lithium hydride is very sluggish.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14515

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