55776-34-6Relevant academic research and scientific papers
Decarbonylative radical coupling of α-aminoacyl tellurides: Single-step preparation of γ-amino and α,β-diamino acids and rapid synthesis of gabapentin and manzacidin A
Nagatomo, Masanori,Nishiyama, Hayato,Fujino, Haruka,Inoue, Masayuki
supporting information, p. 1537 - 1541 (2015/01/30)
A new radical-based coupling method has been developed for the single-step generation of various γ-amino acids and α,β-diamino acids from α-aminoacyl tellurides. Upon activation by Et3B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (-)-manzacidin A.
Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to C{double bond, long}N double bonds
Cougnon, Fabien,Feray, Laurence,Bazin, Samantha,Bertrand, Michèle P.
, p. 11959 - 11964 (2008/03/13)
Diethylzinc-mediated radical addition to C{double bond, long}N bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as rea
Aqueous phase one-electron reduction of sulfonium, selenonium and telluronium salts
Eriksson, Per,Engman, Lars,Lind, Johan,Merenyi, Gabor
, p. 701 - 705 (2007/10/03)
Triorganylsulfonium, -selenonium and -telluronium salts were reduced by carbon dioxide radical anions/solvated electrons produced in aqueous solution by radiolysis. The radical expulsion accompanying reduction occurred with the expected leaving group propensities (benzyl > secondary alkyl > primary alkyl > methyl > phenyl), although greater than expected loss of the phenyl group was often observed. Diorganyl chalcogenides formed in the reductions were conveniently isolated by extraction with an organic solvent. Product yields based on the amount of reducing radicals obtained from the γ-source were often higher than stoichiometric (up to 1800 %) in the reduction of selenonium and telluronium compounds; it is likely that this result can be accounted for in terms of a chain reaction with carbon-centred radicals/formate serving as the chain transfer agent. The product distribution was essentially independent of the reducing species for diphenyl alkyl telluronium salts, whereas significant variations were seen for some of the corresponding selenonium salts. This would suggest the intermediacy of telluranyl radicals in the one-electron reduction of telluronium salts. However, pulse radiolysis experiments indicated that the lifetimes of such a species (the triphenyltelluranyl radical) would have to be less than 1 μs. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Reversibility in free-radical reactions of aryltellurides with tributylstannyl, tributylgermyl and tris(trimethylsilyl)silyl radicals
Schiesser, Carl H.,Skidmore, Melissa A.
, p. 145 - 157 (2007/10/03)
1H, 13C, 29Si, 77Se, 119Sn and 125Te NMR spectroscopies reveal that methyl, primary and secondary alkyl radicals, generated through the reaction of aryltelluroalkanes (4-9) with tributyltin hydride, tributylgermanium hydride or tris(trimethylsilyl)silane) under standard radical conditions (benzene, AIBN) are capable of displacing tributylstannyl, tributylgermyl and tris(trimethylsilyl)silyl radicals from aryltellurotributylstannanes (1, 2), aryltellurotributylgermanes (10, 11) and aryltellurotris(trimethylsilyl)silanes (13, 14) respectively. These observations are in agreement with high-level ab initio molecular orbital studies. Calculations using a (valence) double-ζ pseudopotential basis set supplemented with polarization functions and with the inclusion of electron correlation (MP2/DZP) predict energy barriers for the displacement of stannyl (SnH3), germyl (GeH3) and trisilylsilyl ((H3Si)3)Si) radicals by methyl, ethyl and iso-propyl radicals to lie between 22 and 39 kJ mol-1, with reverse barriers of between 12 and 40 kJ mol-1. Consequently, the use of aryltellurides as alkyl radical precursors together with (standard) chain-carrying reagents such as tributyltin hydride, tributylgermanium hydride and tris(trimethylsilyl)silane may be complicated with equilibria which may result in diminished reaction yields.
Substituent Effects and Stereochemistry in 125Te NMR Spectroscopy. Diorganyltellurium Dihalides and Some Tellurides and Ditellurides
Duddeck, Helmut,Biallass, Armin
, p. 303 - 311 (2007/10/02)
125Te, 19F and 13C NMR data for 33 compounds containing tellurium substituents are presented.The 125Te chemical shifts in (PhTeCl2)R compounds are between δ=878 and 1023; in corresponding (PhTeF2)R compounds they are 220 to 360 ppm larger.Effects of subst
The Reaction of Some Substituted ortho-Benzoquinones with Elemental Tellurium and with Tellurium(II) Compounds
Annan, Theodore A.,Ozarowski, Andrew,Tian, Zhigang,Tuck, Dennis G.
, p. 2931 - 2938 (2007/10/02)
The oxidation of elemental tellurium by three ortho-benzoquinones (RO2: R = Cl4C6, Br4C6 or 3,5-ButH2C6) is a direct route to the corresponding tellurium(IV) catecholates Te(O2R)2.The analogous reaction with organotellurium(II) TeR'2 R' = Me2,
Preparation and characterization of ethyl aryl tellurides and their derivatives
Sandhu, A.,Bhasin, K. K.,Verma, R. D.
, p. 1178 - 1181 (2007/10/02)
Ethyl aryl tellurides have been conveniently prepared in high yields by the reaction of aryl tellurolate anions, generated in situ with ethyl bromide.These tellurides have been converted into their respective tellurium dichlorides which on further treatme
