Mercury(II) trifluoroacetate-mediated cyclisation of aryl allenic ethers
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
More filters
14 Mar 2008
TL;DR: InChI as mentioned in this paper ] is a mercury compound that is easily absorbed through the skin and is corrosive; exposure to all mercury compounds is to be strictly avoided; use in a fume hood to protect from light.
Abstract: [13257-51-7] C4F6HgO4 (MW 426.63)
InChI = 1S/2C2HF3O2.Hg/c2*3-2(4,5)1(6)7;/h2*(H,6,7);/q;;+2/p-2
InChIKey = WMHOESUUCMEQMS-UHFFFAOYSA-L
(oxymercuration3 and aminomercuration17 of alkenes; polyene cyclization;21 allylic oxidation;32 macrolide synthesis37)
Alternate Name: mercuric trifluoroacetate.
Physical Data: mp 171–173 °C.
Solubility: sol THF, DME, dioxane; insol hexane.
Preparative Methods: can be prepared from Mercury(II) Oxide in Trifluoroacetic Acid2-4 or generated in situ from Mercury(II) Acetate and CF3CO2H.8b
Form Supplied in: white, hygroscopic crystals.
Handling, Storage, and Precautions: acute poison; is easily absorbed through the skin and is corrosive; exposure to all mercury compounds is to be strictly avoided. Releases toxic Hg fumes when heated to decomposition. Protect from light. Use in a fume hood.
References
More filters
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
110 citations
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
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
39 citations