65815-76-1

Upstream product

• 110-89-4 piperidine 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 50780-50-2 4-chloromethoxycarbonyloxy-1-nitrobenzene 
• 2591-86-8 N-Formylpiperidine 
• 100-02-7 4-nitro-phenol 
• 7693-46-1 4-Nitrophenyl chloroformate 

Relevant academic research and scientific papers

Nucleofugality hierarchy, in the aminolysis reaction of 4-cyanophenyl 4-nitrophenyl carbonate and thionocarbonate. Experimental and theoretical study

Nucleophilic substitution reactions of the title compounds have been investigated with a series of secondary alicyclic amines in several solvents. The solvent, amine, and electrophilic group effects on kinetics, mechanism and nucleofugality hierarchy are discussed from experimental and theoretical studies. These studies show the mechanistic dependence on the solvent polarity; the theoretical results indicate that the relative polarization of the reactive centres (CO and CS) and the stabilization of the nucleofuges are the main factors in the control of the product distribution.

The synthesis of phenyl carbamates catalyzed by iron (II) bromide: An oxidative approach for cross-coupling of phenols with formamides

The carbamate group is a key structural motif in many approved drugs and pro-drugs. There is increasing use of carbamates in the medicinal chemistry and agrochemical industry. We present, reagents and chemical methodologies for the synthesis of carbamates, and recent applications. The direct coupling of simple phenols with mono- and di-alkyl formamides provided the phenylcarbamate products.

Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates

An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro

Structure-reactivity correlations in the aminolysis of aryl chloroformates

The reactions of a series of secondary alicyclic amines with 4-methylphenyl and 4-methoxyphenyl chloroformates are subjected to a kinetic investigation in water, at 25.0°C, ionic strength 0.2 M (KCI). Under amine excess, pseudo-first-order rate coefficients (kobs) are found for all reactions. Plots of kobs vs [NH] (NH is the free amine) are linear, with the slope (kN) pH independent, except the reactions of l-(2-hydroxyethyl)piperazine with both substrates at pH 6.2-7.3. The Broensted-type plots for the kN values for the aminolysis of both chloroformates are linear, with slopes ca. 0.3, which is consistent with rate-determining formation of a zwitterionic tetrahedral intermediate (T±). With the PKa and log kN data for the present reactions, together with those for the same aminolysis of phenyl and 4-nitrophenyl chloroformates, two dual parametric equations are found for log kN as a function of pKa of the nucleophile, Hammett sigma of the "nonleaving" group, and pKa of the "nonleaving" group, with coefficients βN = 0.3, ρnlg = 0.7, and βnlg = -0.2, respectively.

Kinetics and mechanism of the aminolysis of phenyl and 4-nitrophenyl chloroformates in aqueous solution

The reactions of secondary alicyclic amines with phenyl and 4- nitrophenyl chloroformates (PClF and NPClF, respectively) are subjected to a kinetic investigation in aqueous solution, 25.0 °C, ionic strength 0.2 (KCl). The reactions are followed spectropho

α-Haloalkyl Haloformates and Related Compounds 1. A Convenient Synthesis of Carbamates via Chloromethyl Carbamates

The preparation of carbamates under mild conditions utilizing a new class of activated carbonates (containing chloromethyl function) is described.