85121-08-0Relevant academic research and scientific papers
Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
supporting information, p. 3099 - 3103 (2018/05/22)
An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
REGIOSELECTIVITY OF COMPLEXATIONS OF SUBSTITUTED PHENYL BENZOATES AND PHENYL PHENYLACETATES WITH Cr(CO)6
Hrnciar, Pavol,Cernak, Peter,Gajda, Vladimir,Toma, Stefan
, p. 2095 - 2102 (2007/10/02)
Selectivity of complexation of substituted phenyl benzoates is very low.In most cases, comparable yields of both regioisomeric complexes are isolated.Exception is 4-chlorophenyl ester, where benzoic acid moiety is complexed nearly exclusively.Very high regioselectivity of complexation was observed with substituted phenyl phenylacetates.The substituent of substituted phenols has not any effect on the complexation, and only phenylacetic acid moiety is complexed.This observation supports the recently proposed mechanism of the catalytic activity of the esters at arene complexation.
Alkaline Hydrolysis of Aryl Phenylacetates and Aryl 4-Nitrophenylacetates. Evidence consistent with an Elimination-Addition Mechanism
Chandrasekar, Ramamurthy,Venkatasubramanian, Nagaswami
, p. 1625 - 1632 (2007/10/02)
Hydrolysis of the substituted phenyl esters of phenylacetic acid is found to be first order each in the ester and hydroxide ion.Hydrolysis is catalysed by general bases and the catalytic coefficients for the substituted phenoxides obey the Broensted relation with β +0.49.The rate of hydrolysis of the esters of 4-nitrophenylacetic acid is independent of in the range employed.Both series of reactions exhibit low solvent isotope effect and high sensitivity to substituents in the leaving group .These datasuggest an E1cB mechanism for the hydrolysis.The keten intermediate envisaged for such a mechanism has been trapped as the anilide when the reactions are conducted in aniline buffers, without any effect on the rate of hydrolysis for variations in .An increase in the DMSO content in the solvent decreases the rate of hydrolysis of the esters of 4-nitrophenylacetic acid, which is explained by an (E1cB)anion mechanism for the hydrolysis.Transfer to aqueous DMSO results in rate accelerations for the esters of phenylacetic acid which can be accounted for by either an (E1cB)Bion pair or (E1cB)reversible mechanism for the hydrolysis.
