114460-18-3Relevant academic research and scientific papers
Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction
Boy, P.,Combellas, C.,Suba, C.,Thiebault, A.
, p. 4482 - 4489 (2007/10/02)
Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step SRN1 reaction in the presence of a redox mediator starting from aromatic halides and 2,6-di-tert-butyl phenoxide.With monoaryl halides activated by electron-withdrawing substituents (N of pyridyl or quinolyl, trifluoromethyl, cyano, sulfone, ester, ketone, alkyl sulfide, N(1+) of anilinium), biaryls are obtained in good yields (between 50 and 95percent).The yields of ter- and quateraryls are lower (40percent maximum).The reaction is extended to other ortho-disubstituted phenols.Elimination reactions of the tert-butyl groups from the products are achieved by a Friedel-Crafts reaction using either trifluoromethanesulfonic acid or aluminum trichloride as catalysts.
Theory and Experimental Illustration of Preparative Electrochemistry Using Redox Catalysis of Electron Transfer Initiated Radical Chain Reactions. Application to the Cross-Coupling between Aryl Halides and Phenoxide Ions
Alam, N.,Amatore, C.,Combellas, C.,Thiebault, A.,Verpeaux, J. N.
, p. 6347 - 6356 (2007/10/02)
A general equation predicting the yield of electron transfer initiated radical chain reaction (SRN1 and related mechanisms) under preparative electrochemical conditions is given for situations where the electron-transfer activation of the chain is performed by means of a redox mediator.Simple tests, allowing for the choice of proper redox mediator, are given, and their origins established and discussed.The validity and application of this simple model is shown and discussed for the case of the SRN1-like reaction involving di-tert-butylphenoxide as a nucleophile, to afford biaryls of interest for their properties in nonlinear optics.
Selective Electrochemical and Photochemical Syntheses of Unsymmetrical Biaryls and Their Non-linear Optical Properties
Combellas, Catherine,Gautier, Helene,Simon, Jacques,Thiebault, Andre,Tournilhac, Francois,et al.
, p. 203 - 204 (2007/10/02)
A selective synthesis of unsymmetrically substituted electron donor/electron acceptor biaryls is described which is based on an electrochemically or photochemically induced SRN1 reaction; the optical hyperpolarizability coefficients β are determined in solution for the various reaction products and found to be of the same order of magnitude as that of 4-nitro-aniline.
