78823-56-0Relevant academic research and scientific papers
Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups
Kim, Joong-Gon,Jang, Doo Ok
experimental part, p. 2688 - 2692 (2009/08/09)
We developed a simple, efficient, and selective method for preparing organic carbamates and carbonates using a catalytic amount of indium. A wide range of carbamates and carbonates were synthesized in high yields. The method is also applicable to the selective protection of amino groups under mild conditions.
An efficient modification of the Hofmann rearrangement: synthesis of methyl carbamates
Gogoi, Pranjal,Konwar, Dilip
, p. 531 - 533 (2007/10/03)
A series of methyl carbamates was synthesized using NaOCl as an oxidant in the presence of KF/Al2O3/MeOH at reflux in excellent yields.
Trapping of carbamic acid species with (trimethylsilyl)diazomethane
Ito, Yoshikatsu,Ushitora, Hiromi
, p. 226 - 235 (2007/10/03)
Methoxycarbonylation of a variety of amines into the corresponding methyl carbamates was accomplished by allowing them to react with (trimethylsilyl) diazomethane TMSCHN2 under bubbling of CO2. The reaction was performed at room temperature for a period of ca. 2 h in benzene-MeOH (4/1 v/v), which was the solvent of choice. In this mixed solvent, undesirable bicarbonate is formed in equilibrium along with carbamate anion. Owing to the irreversibility in the esterification step by TMSCHN2, however, the yield of methyl carbamate can reach very high.
Synthesis of functionalized carbamates through a palladium-catalyzed reductive carbonylation of substituted nitrobenzenes
Wchman, Petra,Borst, Leo,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.
, p. 13 - 21 (2007/10/03)
The palladium-catalyzed reductive carbonylation of ortho and para-substituted nitrobenzenes has proven to be an attractive route for the synthesis of functionalized carbamates. For the Pd(1,10-phenanthroline)2(triilate}2 catalyst system, the scope of the reaction has been studied. Substrates with electron-donating substituents at the para position were found to decrease the catalytic activity, most probably as a result of their relatively low oxidizing capacity. The selectivity towards the desired carbamate, however, was increased for these substrates. Under the influence of electron-withdrawing substituents the azoxybenzene and azobenzene derivatives became important side products. Introduction of large steric hindrance at the ortho position of the nitro substrates gave rise to an interesting side reaction, viz. methoxylation of the aromatic ring. The methoxylation reaction appeared to occur on an intermediate species in the catalytic cycle. Several functionalities have shown to be resistant to the reaction conditions required for the conversion of the nitro group. Especially with 4-nitrobenzoic acid, an extremely high activity and selectivity was found, thus yielding a very convenient synthesis for N-protected amines containing carboxylic acid functions. VCH Verlagsgesellschaft mbH.
