Addition Of Phthalimide Research Articles

Addition of phthalimide and acetone to phosphorylated methylene quinones

New method for synthesis of phosphorylated methylene quinones via bromination of the sterically hindered phenol [prepared via benzylation of secondary chlorophosphines with 4-(methoxymethyl)-2,6-di-tert-butylphenol] with N-bromosuccinimide followed by dehydrobromination with trimethyl orthoformate has been developed. Tertiary phosphine oxides containing the fragment of sterically hindered phenol and amine or acetonyl group have been synthesized for the first time in the reaction of phosphorylated methylene quinones with N- and C-nucleophiles.

Kinetics and Mechanism of Oxidation of Aniline by N-Bromophthalimide

Kinetics of oxidation of aniline by N-bromophthalimide (NBP) in acetonitrile-water solvent mixture at 303 K in the presence of perchloric acid has been followed iodometrically. The reaction is first order with respect to both aniline and NBP and is catalyzed by H + ion and the order of the reaction with respect to (H + ) is also one. It has been found that the reaction rate is not affected by changes in ionic strength of the reaction medium or by the addition of acrylonitrile and potassium bromide. However, addition of phthalimide causes a decrease in the rate of reaction. An increase in the water content of the solvent mixture decreases the rate of reaction. Thermodynamic and activation parameters have also been evaluated.

The use of new chiral phosphite and amidophosphite ligands in the Rh-catalyzed hydrogenation of dehydro-β-amino acid derivatives

New chiral phosphite-type ligands were synthesized. The tests of these ligands in the asymmetric Rh-catalyzed hydrogenation of N-acetyl derivatives of dehydro-β-amino acid esters showed their high enantioselectivity (up to 75% ee). The reaction of nucleophilic addition of phthalimide to disubstituted alkynes offering access to esters of N-phthaloyldehydro-β-amino acids was discovered. Higher conversion and enantioselectivity in the hydrogenation of N-acetyl and N-phtaloyl derivatives of dehydro-β-amino acids were observed in fluorinated alcohols as compared to common organic solvents.

Kinetics and Mechanism of Oxidation of Isoleucine by N‐Bromophthalimide in Aqueous Perchloric Acid Medium

The kinetics of oxidation of isoleucine with N‐bromophthalimide has been studied in perchloric acid medium potentiometrically. The reaction is of first order each in [NBP] and [amino acid] and negative fractional order in [H+]. The rate is decreased by the addition of phthalimide. A decrease in the dielectric constant of the medium increases the rate. Addition of halide ions or acrylonitrile has no effect on the kinetics. Similarly, variation of ionic strength of the medium does not affect the reaction rate. The reaction rate has been determined at different temperatures and activation parameters have been calculated. A suitable mechanism involving hypobromous acid as reactive species has been proposed.

ChemInform Abstract: Dyotropic Rearrangement in Homochiral Organoiron Complexes Resulting in Inversion at Two Adjacent Carbon Centers.

The kinetic products derived from addition of phthalimide, N-methyltoluenesulfonamide, or benzenethiol to homochiral Fp(dioxene)BF 4 salts [Fp=CpFe(CO) 2 ] undergo unimolecular dyotropic rearrangement, resulting in inversion of the two initially formed asymmetric centers

Cs2CO3/[bmim]Br as an Efficient, Green, and Reusable Catalytic System for the Synthesis of N-Alkyl Derivatives of Phthalimide under Mild Conditions

Aza-conjugate addition of phthalimide to α,β-unsaturated esters efficiently achieves in the presence of catalytic amount of Cs2CO3 and ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) under mild reaction conditions (70°C) to afford N-alkyl phthalimides in high yields and relatively short reaction times.

Photoinduced Addition of Phthalimide to Unactivated Alkynes†

Photoexcited phthalimide in equilibrium with its conjugated base produces the regioselective hydrophthalimidation of conjugated alkynes. The vinylphthalimide thus obtained is hydrolyzed to the corresponding carbonyl compound. With unconjugated alkynes, the outcome is a double addition of phthalimide to the triple bond. The reaction is assumed to take place via single electron transfer from either the alkyne or the phthalimide anion to the excited phthalimide as the primary photoprocess.

An improved diphosphine-iridium(I) catalyst system for the asymmetric hydrogenation of cyclic imines: Phthalimide as an efficient co-catalyst

Abstract The asymmetric hydrogenation of cyclic ketimines, 1-alkyl-3,4-dihydroisoquinolines 5a,b , was carried out with diphosphine-iridium(I) complex catalysts in the presence of various imides or amides as a co-catalyst. Remarkable effects of five-membered imides on the enantioselectivity and the catalytic activity were observed. The enantioselectivity with a BCPM 1 -iridium(I) complex was much improved up to 93% ee by addition of phthalimide.

Dyotropic rearrangement in homochiral organoiron complexes resulting in inversion at two adjacent carbon centers

The kinetic products derived from addition of phthalimide, N-methyltoluenesulfonamide, or benzenethiol to homochiral Fp(dioxene)BF 4 salts [Fp=CpFe(CO) 2 ] undergo unimolecular dyotropic rearrangement, resulting in inversion of the two initially formed asymmetric centers

Synthesis of nitrogen-15-labeled amino sugar derivatives by addition of phthalimide- 15N to a carbohydrate epoxide

Derivatives of methyl 2-amino-2-deoxy-α- d-altropyranoside- 2- 15 N and methyl 3-amino-3-deoxy-α- d-glucopyranoside- 3- 15 N have been synthesized by addition of phthalimide- 15 N to methyl 2,3-anhydro-4,6- O-benzylidene-α- d-allopyranoside. The structures of the phthalimido derivatives that resulted have been proved chemically, by conversion into known aminodeoxy derivatives, and spectroscopically, by 1H- and 13C-n.m.r. spectroscopy. 1H-N.m.r. spectroscopy at 360 MHz also allowed definition of the configurations and conformations of the labeled and unlabeled phthalimido derivatives, and the measurement of vicinal 1H— 15N coupling-constants that are characteristic of 1H— 15N dihedral angles of ∼60°.