143565-02-0Relevant articles and documents
Palladium-Mediated Reactions of Chloroformates with Phenylselenotris(trimethylsilyl)silane and Aryltellurotris(trimethylsilyl)silane: Improved Procedure for the Preparation of (Phenylseleno)- and (Aryltelluro)formates
Schiesser, Carl H.,Skidmore, Melissa A.
, p. 5713 - 5715 (2007/10/03)
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Photoinduced free radical chemistry of the acyl tellurides: Generation, inter- and intramolecular trapping, and ESR spectroscopic identification of acyl radicals
Crich, David,Chen, Chen,Hwang, Jae-Taeg,Yuan, Hongwei,Papadatos, Aristotle,Walter, Robert I.
, p. 8937 - 8951 (2007/10/02)
Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-α-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are α-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords α-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the α-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields α-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.
The Chemistry of Acyl Tellurides: Generation and Trapping of Acyl Radicals, Including Aryltellurium Group Transfer
Chen, Chen,Crich, David,Papadatos, Aristotle
, p. 8313 - 8314 (2007/10/02)
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