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Journal ArticleDOI

Mercury(II) trifluoroacetate-mediated cyclisation of aryl allenic ethers

04 Nov 1991-Tetrahedron Letters (Pergamon)-Vol. 32, Iss: 45, pp 6641-6644
TL;DR: Mercury(II) trifluoroacetate brings about a facile cyclisation of aryl allenic(aryl 2,3-butadien-1yl) ethers to 4-methyl-2H-1-benzopyrans.
About: This article is published in Tetrahedron Letters.The article was published on 1991-11-04. It has received 17 citations till now. The article focuses on the topics: Aryl & Mercury (element).
Citations
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Journal ArticleDOI
TL;DR: Simple and mild methods for the synthesis of allenes, employing indium- and zinc-mediated dehalogenation reactions of vicinal dihalides in an aqueous solvent, are described.
Abstract: Simple and mild methods for the synthesis of allenes, employing indium- and zinc-mediated dehalogenation reactions of vicinal dihalides in an aqueous solvent, are described. By using these procedures, various allenylmethyl aryl ethers and monosubstituted allenes have been prepared in good to excellent yields.

10 citations

Journal ArticleDOI
TL;DR: In this article, a three-step sequence for conversion of substituted phenyl carbamide into 1-cyano-4-methylidene -1,2,3,4-tetrahydro quinoline involving N-propargylation, allene formation followed by mercury (II) trifluoro acetate catalysed cyclization is described.

10 citations

Journal ArticleDOI
TL;DR: In this article, aryl allenylmethyl ethers with tris(4-bromophenyl)aminium hexachloroantimonate in acetonitrile at room temperature were treated with a facile cation radical induced Claisen rearrangement to yield 2-(o-hydroxyaryl)buta-1,3-dienes.
Abstract: Treatment of aryl allenylmethyl ethers with tris(4-bromophenyl)aminium hexachloroantimonate in acetonitrile at room temperature induces a facile cation radical induced Claisen rearrangement to yield 2-(o-hydroxyaryl)buta-1,3-dienes.

9 citations

Journal ArticleDOI
TL;DR: In this paper, aryl allenylmethyl ethers in diethylene glycol were rearranged to yield 2-(o-hydroxyaryl)buta-1,3-dienes and 4-methyl-2H-1-benzopyrans.
Abstract: Thermal Claisen rearrangement of aryl allenylmethyl ethers in diethylene glycol afforded 2-(o-hydroxyaryl)buta-1,3-dienes and 4-methyl-2H-1-benzopyrans in good yield.

8 citations

Journal ArticleDOI
TL;DR: Linked scans, high-resolution mass spectrometry, collision-activated dissociation-B/E linked-scan spectra, and D-labeling have been employed to support the proposed mechanisms and ion structures.

6 citations

References
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Journal ArticleDOI
TL;DR: Le (bis-[(bromo-4 di-t-butyl-2,6)phenoxy methyl) aluminium peut etre utilise pour obtenir l'isomere (Z) alors que l'sisomeres (E) est produit avec le (bis-(diphenyl 2,6 phenoxy] methyl) aluminum as discussed by the authors.
Abstract: Le (bis-[(bromo-4 di-t-butyl-2,6)phenoxy methyl) aluminium peut etre utilise pour obtenir l'isomere (Z) alors que l'isomere (E) est produit avec le (bis-[diphenyl-2,6 phenoxy] methyl) aluminium

113 citations

Journal ArticleDOI
TL;DR: This is the first to show that meta-Claisen rearrangement occurs preferentially even when a free para position is available, and can be interpreted in terms of the small bond energy of the breaking apical carbon-iodine (III) bond.
Abstract: Reported for the first time are the generation of allenyliodinanes and their reductive iodonio-Claisen rearrangement Reaction of propargylsilanes, germanes, and stannanes with aryliodinanes in the presence of BF 3 -Et 2 O undergoes a reductive iodonio-Claisen rearrangement under mild conditions, yielding o-propargyliodoarenes in good yields The reductive ortho propargylation probably involves the intermediate formation of allenyl(aryl) iodinanes, which undergo [3,3]-sigmatropic rearrangement The lack of crossover products argues for the intramolecularity of the rearrangement When both ortho positions of aryliodinanes are occupied with alkyl substituents, the reductive iodonio-Claisen rearrangement affords meta substitution products This is the first to show that meta-Claisen rearrangement occurs preferentially even when a free para position is available The reductive ortho propargylation of iodinanes takes place under much milder conditions than the Claisen rearrangement The lower activation energy associated with the iodonio-Claisen rearrangement of allenyl(aryl) iodinanes can be interpreted in terms of the small bond energy of the breaking apical carbon-iodine (III) bond

65 citations

Journal ArticleDOI
TL;DR: Les cyclisations sont obtenues par reaction avec la piperidine ou la triethylamine in presence of a catalyseur au palladium as discussed by the authors.
Abstract: Les cyclisations sont obtenues par reaction avec la piperidine ou la triethylamine en presence d'un catalyseur au palladium: obtention d'heterocycles azotes ou oxygenes a 5, 6 ou 7 chainons

64 citations