81609-27-0Relevant academic research and scientific papers
Conversion of (sp3)C-F bonds of alkyl fluorides to (sp 3)C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents
Begum, Shameem Ara,Terao, Jun,Kambe, Nobuaki
, p. 196 - 197 (2008/02/03)
A convenient method for conversion of (sp3)C-F bonds to (sp 3)C-Z (Z = I, SR, SeR, TeR) bonds has been developed. The reaction proceeds at room temperature using magnesium salts (Z-MgX). SN2 mechanism for substitiution of primary alkyl fluorides with MgI2 in ether was supported by the inversion of the stereochemistry of the carbon connecting to F. Copyright
Conversion of a (sp3)C-F bond of alkyl fluorides to (sp 3)C-X (X = Cl, C, H, O, S, Se, Te, N) bonds using organoaluminium reagents
Terao, Jun,Begum, Shameem Ara,Shinohara, Yoshiaki,Tomita, Masahiro,Naitoh, Yoshitaka,Kambe, Nobuaki
, p. 855 - 857 (2007/10/03)
A simple method for the conversion of (sp3)C-F bonds of alkyl fluorides to (sp3)C-X (X = Cl, C, H, O, S, Se, Te, N) bonds has been achieved by the use of a hexane solution of organoaluminum reagents having Al-X bonds. The Royal Society of Chemistry.
Rate Constants for Chalcogen Group Transfers in Bimolecular Substitution Reactions with Primary Alkyl Radicals
Curran, Dennis P.,Martin-Esker, Amanda A.,Ko, Sung-Bo,Newcomb, Martin
, p. 4691 - 4695 (2007/10/02)
Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio)phthalimide and from Me2S2 and Ph2S2 to primary alkyl radicals, have been determined by competition kinetics using PTOC esters as the radical precursors and competing trapping agents.Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the symmetrical disulfide, and the rate constant for PhSe group transfer from PhSeSePh isgreater than those from the derivatives studied here.Substituent effects suggest that the chalcogen transfer reactions may be concerted.For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approximately equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same.The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chemistry.
Oxygen-Induced Transmetallation of Organoboranes with Diphenyl Ditelluride
Abe, Taro,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1671 - 1674 (2007/10/02)
Diphenyl ditelluride rapidly reacted with trialkylboranes in the presence of oxygen to give alkyl phenyl tellurides in high yields.The facile rection proceeds via a free-radical mechanism induced by a stoichiometric amount of oxygen.A combination of this transmetallation with hydroboration provides an alternative method for hydrotelluration of olefins.
