Tandem thia-Fries rearrangement--cyclisation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate benzyne precursors.
نویسندگان
چکیده
A novel transformation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate aryne precursors is described.
منابع مشابه
A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles
The synthesis of C3-carbocyclic spirooxindoles was realized by way of an intramolecular [2 + 2] cycloaddition reaction between a vinylidene indolin-2-one and an alkyne. The cycloaddition reaction occurs selectively with the distal double bond of the allene, is tolerant of a phenyl and trimethylsilyl group on the terminus of the alkyne, and can be used to access bicyclo[4.2.0]octadienes and bicy...
متن کاملThe Hexadehydro-Diels–Alder Reaction: A New Chapter in Aryne Chemistry
Arynes continue to stimulate new reactions and theoretical insight in aromatic chemistry. This has been driven in recent years by the exceptional versatility of 2-(trimethylsilyl)phenyl triflate (1) as a precursor to ortho-benzyne. Such compounds react under mild conditions and have enabled a substantial development of aryne chemistry both in terms of classical transformations (nucleophilic add...
متن کاملUnanticipated formation of ortho-sulfone substituted phenols by anionic thia-Fries rearrangement of (aryl triflate)tricarbonylchromium complexes.
Tricarbonylchromium complexes of aryl triflates undergo base-mediated anionic thia-Fries rearrangements to generate push-pull substituted [ortho-hydroxyaryl(trifluoromethylsulfonyl)phenol]tricarbonylchromium complexes under very mild reaction conditions.
متن کاملStereoselective synthesis of 2-S-phenyl-2-deoxy-beta-glycosides using phenyl 2,3-O-thionocarbonyl-1-thioglycoside donors via 1,2-Migration and concurrent glycosidation.
[figure: see text] 1,2-Migration and concurrent glycosidation of phenyl 2,3-O-thionocarbonyl-1-thlo-alpha-L-rhamnopyranosides under the action of methyl trifluoromethanesulfonate (MeOTf) afforded in high yields the 3-O-(methylthio)carbonyl-2-S-phenyl-2,6-dideoxy-beta-L-glucopyranosides, ready precursors to the corresponding 2-deoxy-beta-glycosides.
متن کاملSolvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations
The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.
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ورودعنوان ژورنال:
- Chemical communications
دوره 49 69 شماره
صفحات -
تاریخ انتشار 2013