Topic
Boron tribromide
About: Boron tribromide is a research topic. Over the lifetime, 546 publications have been published within this topic receiving 5946 citations. The topic is also known as: Boron bromide & Tribromoborane.
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TL;DR: The use of boron tribromide for effecting complete demethylation of aryl methyl ethers at, or below, room temperature was described in this article.
477 citations
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TL;DR: A formal synthesis of roseophilin, a pentacyclic structure possessing significant antitumor activity, starting from 3-cycloundecenylcarboxylic acid has been completed as discussed by the authors.
Abstract: A formal synthesis of roseophilin, a novel pentacyclic structure possessing significant antitumor activity, starting from 3-cycloundecenylcarboxylic acid has been completed. The acid was converted diastereoselectively to the corresponding menthol ester via the ketene which, in turn, provided (S)-3-cycloundecenylcarboxaldehyde. Diastereoselective propargylation with propargyltriphenylstannane promoted by an asymmetric boron reagent prepared in situ from boron tribromide and the bis-p-toluenesulfonamide of (S,S)-stilbenediamine gave (1S,1‘R)-1-cycloundec-2‘-enylbut-3-yn-1-ol which set the stage for the key metathesis reaction. Platinum-catalyzed enyne metathesis via a formal [2 + 2] cycloaddition to a cyclobutene followed by conrotatory ring opening created the corresponding bicyclo[10.2.1]pentadeca-1(15),2-diene. Regioselective epoxidation of the less reactive double bond of the 1,3-diene was accomplished by 1,4-bromohydrin formation followed by base. Cuprate opening regio- and stereospecifically installed...
146 citations
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129 citations
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103 citations
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TL;DR: In fluorous triphasic reactions, such as bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide, the middle fluorous phase acts as a liquid membrane permitting passive transport of the reagents to the top layer involving the substrates, thereby regulating the reactions.
Abstract: In fluorous triphasic reactions, such as bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide, the middle fluorous phase acts as a liquid membrane permitting passive transport of the reagents at the bottom to the top layer involving the substrates, thereby regulating the reactions.
90 citations