75250-50-9Relevant academic research and scientific papers
New Aspects of the Telluroxide Elimination. A Facile Elimination of sec-Alkyl Phenyl Telluroxide Leading to Olefins, Allylic Alcohols, and Allylic Ethers
Uemura, Sakae,Fukuzawa, Shin-ichi
, p. 2748 - 2752 (2007/10/02)
The utility of the telluroxide for olefin synthesis, a reaction which previously appeared to be of little value, is described.Treatment of sec-alkylphenyltellurium dibromides, except for the cyclohexyl system, with aqueous NaOH at room temperature affords olefins, allylic alcohols, and/or allylic ethers in high yields presumably via the formation of sec-alkyl phenyl telluroxides and their facile telluroxide elimination.As to the formation of linear olefins, more preference for elimination toward the less substituted carbon was observed than the selenoxide and sulfoxide eliminations.In the cyclododecyl case only trans-cyclododecene was formed as an olefin component in a sharp contrast to the selenoxide elimination that affords a 1:1 mixture of cis and trans isomers.On the contrary, in the n-alkyl and cyclohexyl cases the corresponding telluroxides are stable compounds that afford similar elimination products including vinylic ethers only by neat pyrolysis at temperatures above 200 deg C.
Organic Tellurium and Selenium Chemistry. Reduction of Tellurides, Selenides, and Selenoacetals with Triphenyltin Hydride
Clive, Derrick L. J.,Chittattu, Gim J.,Farina, Vittorio,Kiel, William A.,Menchen, Steven M.,et al.
, p. 4438 - 4447 (2007/10/02)
Preparative and mechanistic details are described for the conversion of selenides into hydrocarbons RH> by heating with triphenyltin hydride at about 120 deg C.The process has been extended to selenoacetals in a form that constitutes a reduction methods for carbonyl compounds RR'C(SePh)2 -> RR'CH2>.Selective reduction of selenoacetals in the presence of thioacetals is possible.Cold-labeled species can be prepared by using triphenyltin deuteride.Tellurides are available easily without problems arising from exposure to air provided that the work is done in a photographic darkroom equipped with a red safety light.These tellurides, as well as the corresponding dichlorides , are reduced under very mild conditions (25-80 deg C) by triphenyltin hydride.The selenium- and tellurium-based chemistry has been used for the unusual process of reducing an epoxide in the presence of a ketone carbonyl.
