Showing papers on "Boron tribromide published in 2004"
TL;DR: The physicochemical results were in accordance to establish the compounds hydroxylated on C-6 and C-7 positions as the most active of the series with antioxidant potencies comparable to those of quercetin and vitamin C.
53 citations
TL;DR: A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed, and it is shown that under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl Ethers are also cleaved more rapidly than Propargyl.
43 citations
TL;DR: In this article, the treatment of 2(or 4)-benzylamino substituted quinolines with BBr3 yields the corresponding amino or hydroxy substituted compounds, and the scope and limitations of this novel reaction are discussed.
29 citations
TL;DR: In this paper, the silyl ligand Cp*(CO)2FeSiMe2R (Cp* = C5Me5, R = Me and Ph) with 1 equiv of BBr3 at room temperature was treated with bromodemethylation.
7 citations
TL;DR: In this paper, a mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed, where boron tribromide is used to cleave aryl methyl ethers and esters.
Abstract: Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed. [reaction: see text]
2 citations
Journal Article•
1 citations
TL;DR: In this paper, a 2-substituted cyclobutanone acetal was synthesized from their corresponding cyclobutanes and subsequently treated with boron tribromide.
Abstract: Nine 2-substituted cyclobutanone acetals, in addition to the parent cyclobutanone acetal, were synthesized from their corresponding cyclobutanones and subsequently treated with boron tribromide. The substituents were either alkyl chains or a phenyl and a benzyl group, respectively. The major compounds obtained in these reactions were, in most cases, the geminal dibromocyclobutanes which were obtained in yields between 50 and 73%. A 2-fold excess of BBr3 and a reaction time of 3 h at −78 °C afforded the best yields. In four cases no dibromide formation was observed at all, and the cyclobutanone acetals were hydrolyzed to the corresponding cyclobutanone. This is probably due to increased steric hindrance of the acetal and BBr3 in the transition state.