37606-77-2Relevant academic research and scientific papers
Neryl- and geranyltriethylammonium halides in the allylation of sodium diethyl malonate. The effect of the leaving group of the allylating reagent on the selectivity of the reaction
Petrushkina, E. A.,Zakharkin, L. I.
, p. 249 - 251 (2007/10/02)
In the absence of catalyst, N-neryl- and N-geranyltriethylammonium halides can allylate sodium ethyl malonate to give terpene malonate derivatives.Using the above-mentioned amonium salts, geranyl and neryl acetates, geranyl ethyl carbonate, and geranyl diethyl phosphate as examples, it has been shown that with Pd0 and PdII catalysts, the selectivity of formation of neryl-, geranyl-, and linalylmalonates can be governed by varying the leaving group of the allylating agent. - Key words: palladium, complexes, catalysis, sodium diethyl malonate, allylation.
REACTIONS OF TITANIUM DERIVATIVES OF SOME CH-ACIDS WITH CARBONYL COMPOUNDS. IV. SYNTHESIS AND SOME TRANSFORMATIONS OF DERIVATIVES OF (2-ALKENYLIDENE)MALONIC ACIDS
Kasatkin, A.N.,Biktimirov, R.Kh.,Kulak, A.N.,Tolstikov, G.A.
, p. 613 - 620 (2007/10/02)
Ester and nitrile derivatives of (2-alkylidene)malonic acids, obtained by the condensation of (i-PrO)3Ti derivatives of CH2(CO2Et)2, CH2(CN)CO2Et, and CH2(CN)2 with α,β-unsaturated aldehydes, react with NaBH4 and RMgX to give esters and nitriles of the corresponding allylmalonic acids.These reactions are accompanied by complete retention of the geometry of the residual double bonds.The reaction of diethyl (2-alkenylidene)malonates with PhCO3H leads to the selective formation of monoepoxides and does not affect the α,β-double bond.
Highly Stereoselective Palladium(0)-Catalyzed Allylation of Active Methylene Compounds with Allyl Imidates under Neutral Conditions
Suzuki, Osamu,Inoue, Seiichi,Sato, Kikumasa
, p. 239 - 243 (2007/10/02)
In the presence of a catalytic amount of Pd(0), active methylene compounds were allylated by allyl imidates under neutral conditions.In allylation with 3,3-disubstituted allyl imidates, e.g., geranyl and neryl imidate the effect of solvent and ligand to the E/Z ratio are investigated.The reaction in dimethyl sulfoxide by addition of diphosphine, e.g., 1,2-bis(diphenylphosphino)ethane, or large excess of triphenylphosphine as additive ligand gave best results.In these conditions, various active methylene compounds were allylated stereoselectively, especially complete retention of starting olefin geometry was achieved with neryl imidate.
Allylation of Active Methylene Compounds with Allyl Oxime Carbonates Catalyzed by Pd(0)
Suzuki, Osamu,Hashiguchi, Yoshiharu,Inoue, Seiichi,Sato, Kikumasa
, p. 291 - 294 (2007/10/02)
Allylation of active methylene compounds catalyzed by a palladium(0)-phosphine system took place highly stereoselectively by employing allyl oxime carbonates as the allylating reagent.
Etude de l'allylation, catalysee par le nickel, d'enolates stables, par les ethers et les alcools allyliques
Alvarez, Eleuterio,Cuvigny, Therese,Julia, Marc
, p. 199 - 212 (2007/10/02)
The allylation of stable enolates derived from diethyl malonate and ethyl cyanoacetate by a variety of aliphatic or aromatic allylic ethers and by allylic alcohols, under nickel catalysis, was investigated.The influence of ligands, solvents and temperature was studied.
SUBSTITUTIONS CATALYSEES AU NICKEL D'ACETATES ET DE SULFONES ALLYLIQUES
Cuvigny, Therese,Julia, Marc
, p. 383 - 408 (2007/10/02)
The allylic substitution of stable enolates derived from diethyl malonate, ethyl cyanoacetate, ethyl benzylsulfonylacetate, bis(benzenesulfonyl)methane and sodium p-toluenesulfinate by a variety of allylic esters and sulfones has been investigated.Suitable ligands and reaction conditions have been found to ensure high yields, and in some cases considerable control of the regioselectivity of the reaction.
ETUDE DE LA REGIOSELECTIVITE DE LA SUBSTITUTION DES CARBANIONS PAR DES DERIVATIVES ALLIQUES CATALYSEE AU PALLADIUM. OBTENTION SELECTIVE DE COMPOSES A CARBONE QUATERNAIRE
Cuvigny, Therese,Julia, Marc,Rolando, C.
, p. 395 - 414 (2007/10/02)
The influence of the leaving groups, carbanions and ligands on ?-allylpalladium has been investigated in the substitution of primary or tertiary terpene derivatives.Conditions have been found under which the substitution takes place essentially at one or the other end of the allylic system.This provides a new and convenient way to obtain compounds with quaternary carbon atoms, which has been exemplified by the synthesis of 3,3-dimethyl-4-pentenenitrile.
