33183-38-9Relevant academic research and scientific papers
Nucleophilic Substitution Reactions of Trimethylsilylmethyl Arenesulfonates with Anilines and Benzylamines in Acetonitrile
Oh, Hyuck Keun,Shin, Chul Ho,Lee, Ikchoon
, p. 2411 - 2414 (2007/10/02)
The results of kinetic studies on the reactions of trimethylsilylmethyl arenesulfonates, 1 (Me3SiCH2OSO2C6H4Z), with anilines and benzylamines in acetonitrile at 65.0 deg C are reported.The relatively large positive value of the cross-interaction constant between substituents in the nucleophile (X) and leaving group (Z), ρxz, indicates that the reaction proceeds by a SN2 process with a relatively tight transition state.The enhanced rate of 1 compared with the rates for other corresponding carbon analogues leads us to conclude that the destabilizing effect of the α-silyl group on the ground state of 1 due to geminal interaction is important not only for SN1 but also for SN22 reactivities.
ONE-POT CHEMOSELECTIVE REDUCTIVE ALKYLATION OF NITROARENES: A NEW GENERAL METHOD OF SYNTHESIS OF ALKYLANILINES.
Bartoli, Giuseppe,Bosco, Marcella,Pozzo, Renato Dal,Petrini, Marino
, p. 4221 - 4226 (2007/10/02)
A New facile and general synthesis of alkylanilines by one-pot reductive alkylation of nitroarenes is reported.This method is based on the "in situ" reduction by hydrides (LiAlH4 or NaBH4) in the presence of catalytic amounts of Pd/C, of nitronate adducts arising from the conjugate addition of Grignard reagents to mononitroarenes.LiAlH4 showed to be a more efficient but less selective reducing agent than NaBH4.The reaction can be successfully applied to mono, homo and hetero bicyclic systems and allows to introduce a large variety of alkyl chains without isomerisation phenomena.
