67698-82-2Relevant articles and documents
Facile Hydrogenolysis of C(sp3)–C(sp3) σ Bonds
Fillion, Eric,Beaton, Eric,Nguyen, Yen,Wilsily, Ashraf,Bondarenko, Ganna,Jacq, Jér?me
supporting information, p. 3422 - 3434 (2016/11/13)
The modification of benzylic quaternary, tertiary, and secondary carbon centers through palladium-catalyzed hydrogenolysis of C(sp3)–C(sp3) σ bonds is presented. When benzyl Meldrum's acid derivatives bearing quaternary benzylic centers are treated under mild hydrogenolysis conditions – palladium on carbon and atmospheric pressure of hydrogen – aromatics substituted with tertiary benzylic centers and Meldrum's acid are obtained with good to excellent yield. Analogously, substrates containing tertiary or secondary benzylic centers yield aromatics substituted with secondary benzylic centers or toluene derivatives, respectively. Furthermore, this strategy is used for the high yielding synthesis of diarylmethanes. The scope of the reductive dealkylation reaction is explored and the limitations with respect to steric and electronic factors are determined. A mechanistic analysis of the reaction is described that consisted of deuterium labelling experiments and hydrogenolysis of enantioenriched derivatives. The investigation shows that the C(sp3)–C(sp3) σ bond-cleaving events occur through a hybrid SN1/SN2 mechanism, in which the palladium center displaces a carbon-based leaving group, namely Meldrum's acid, with inversion of configuration, followed by reductive elimination of palladium to furnish a C?H bond. (Figure presented.).
Copper-catalyzed hydroxylation of aryl halides with tetrabutylammonium hydroxide: Synthesis of substituted phenols and alkyl aryl ethers
Paul, Rajesh,Ali, Md Ashif,Punniyamurthy, Tharmalingam
supporting information; experimental part, p. 4268 - 4272 (2011/02/25)
The selective hydroxylation of aryl iodides and aryl bromides with tetrabutylammonium hydroxide pentahydrate is described. For this, the combination of copper(I) iodide and 8-hydroxyquinaldine at 70-130C in a mixture of dimethyl sulfoxide and water (2:3) is used. The resultant phenols can be readily reacted with alkyl and allyl halides in situ to provide the corresponding alkyl or allyl aryl ethers in high yields. The reactions are simple, general, and efficient, affording substituted phenols and alkyl aryl ethers under aerobic conditions
Alkoxylated p-phenylenevinylene oligomers: Synthesis and spectroscopic and electrochemical properties
Ndayikengurukiye, Henri,Jacobs, Sven,Tachelet, Wim,Van Der Looy, Johan,Pollaris, Anne,Geise, Herman J.,Claeys, Magda,Kauffmann, Jean M.,Janietz, Silvia
, p. 13811 - 13828 (2007/10/03)
Twenty-one n-alkoxy substituted phenylenevinylene oligomers were synthesized, varying in size, number and position of the OR groups. IR,MS and solubility data are presented. NMR measurements provided the molecular structure as well as information about conformations and molecular dynamics. UV and of cyclic voltammetric data give correlations of chemical structure (number and position of OR substituents) with separate HOMO and LUMO energies.