83867-97-4Relevant academic research and scientific papers
Addition of organolithium reagents to cinnamic acids
Aurell, Maria Jose,Banuls, Maria Jose,Mestres, Ramon,Munoz, Elena
, p. 831 - 846 (1999)
Reaction of tert-butyllithium with p- and m-substituted cinnamic acids at low temperature affords mixtures of 1,4- and 1,3-addition products, whose composition depend on the nature of the substituents. Electron-donating and electron-withdrawing groups favour 1,4- and 1,3-additions, respectively. Linear correlations are obtained with electronic effect and with radical substituent constants.
REGIOSPECIFIC ADDITION OF ORGANOCOPPER REAGENTS TO α,β-UNSATURATED ESTERS
Behforouz, Mohammad,Curran, Timothy T.,Bolan, Joseph L.
, p. 3107 - 3110 (2007/10/02)
Mixed cuprates ArSCu(RMgX)n add rapidly to crotonates and cinnamates to give high yields of Michael adducts.Cuprates of methyl, ethyl, isopropyl, t-butyl, phenyl and vinyl were used.Crotonates give much higher yields of adducts with cuprates using 2-methoxythiophenoxide as a ligand than with those using thiophenoxide.
Contrasting behaviour of (E)-3-(trimethylsilyl)- and (E)-3-phenylpropenoic acids towards n-butyl- and tert-butyllithium
Kruithof, K. J. H.,Mateboer, A.,Schakel, M.,Klumpp, G. W.
, p. 62 - 65 (2007/10/02)
The title compounds 2 and 9 react with tert-buthyllithium to give considerable amounts of 'anti-Michael' adducts 3 and 10, respectively, in which the tert-butyl group is bonded to C-2.A single-electron-transfer (SET) mechanism is proposed for these reacti
