14051-41-3Relevant articles and documents
Activated alkyl- and allyl-alkali metal reagents: Contrasting behaviour towards ethylene
Screttas, Constantinos G.,Steele, Barry R.
, p. 163 - 170 (1993)
Ethylene, hex-1-ene and (+)-α-pinene were readily metallated in methylcyclohexane with the system nBuLi/LiK(OCH2CH2NMe2)2.The regioselectivity of the reaction of metallated hex-1-ene and (+)-α-pinene with CO2 could be substantially modified by the addition of Mg(OCH2CH2OEt)2.Addition of the latter also solubilizes the organometallic reagents.The allylmetallic products from the metallation of hex-1-ene and α-pinene added to ethylene under mild conditions.Whereas up to four molecules of ethylene added to metallated hex-1-ene, only one or two, depending on the reaction ratios, added to metallated α-pinene.Similar reactions involving use of a variety of other strong bases such as nBuLi/tC5H11OK and nBuM (M = Li, Na, K), with and without added TMEDA, indicated that the presence of a tertiary amine, apart from assisting the metallation reaction, is essential for the occurrence of the addition.
Ligand-controlled regiodivergent Ni-catalyzed reductive carboxylation of allyl esters with CO2
Moragas, Toni,Cornella, Josep,Martin, Ruben
supporting information, p. 17702 - 17705 (2015/02/19)
A novel Ni-catalyzed regiodivergent reductive carboxylation of allyl esters with CO2 has been developed. This mild, user-friendly, and operationally simple method is characterized by an exquisite selectivity profile that is dictated by the ligand backbone.
Regioselective Synthesis of β,γ-Unsaturated Acids by the Electrochemical Carboxylation of Allylic Bromides Using a Reactive-metal Anode
Tokuda, Masao,Kabuki, Takashi,Katoh, Yoshitaka,Suginome, Hiroshi
, p. 3345 - 3348 (2007/10/02)
Electrolysis of γ-mono and disubstituted allylic bromides in the presence of atmospheric pressure of carbon dioxide using a platinum cathode and a magnesium anode gave regioselectively the corresponding γ-mono and disubstituted β,γ-unsaturated carboxylic acids in 34-71percent yields.