1541-28-2Relevant academic research and scientific papers
Calcium-catalyzed direct amination of π-activated alcohols
Haubenreisser, Stefan,Niggemann, Meike
supporting information; experimental part, p. 469 - 474 (2011/04/16)
A calcium-catalyzed direct amination of π-activated alcohols with different nitrogen nucleophiles under very mild reaction conditions is presented. The high reactivity of the calcium catalyst allows for an efficient conversion of secondary and tertiary benzylic and allylic as well as tertiary propargylic alcohols. Nitrogen nucleophiles such as carbamates, tosylamides and anilines are readily alkylated at room temperature.
Synthesis of carbamates from diethoxycarbonyl hydrazine derivatives by E1cB eliminative cleavage of the N-N′-bond rather than reduction
Magnus, Philip,Garizi, Negar,Seibert, Kimberly A.,Ornholt, Alexandra
supporting information; experimental part, p. 5646 - 5648 (2010/02/28)
[Chemical Equation Presented] Treatment of diethoxycarbonyl hydrazine derivatives with methyl bromoacetate/Cs2CO3/MeCN at 50°C followed by heating to 80°C resulted in N-N′ bond cleavage to the corresponding carbamates.
Cs2CO3 or CaO as promoters of ethyl N-{[(4-methylphenyl)sulphonyl]oxy}carbamate in amination reactions
Barani, Marco,Fioravanti, Stefania,Pellacani, Lucio,Tardella, Paolo A.
, p. 11235 - 11238 (2007/10/02)
Replacing triethylamine by heterogeneous inorganic bases makes it possible to aminate benzene or other nitrene acceptors, using the title reagent, previously reported to be scarcely reactive. Products of C-H insertion and/or those coming from intermediate aziridines are also obtained.
Improved amination by ethyl n-(4-nitrophenyl)sulphonyloxy carbamate in the presence of inorganic oxides or carbonates
Barani, Marco,Fioravanti, Stefania,Antonietta Loreto,Pellacani, Lucio,Tardella, Paolo A.
, p. 3829 - 3834 (2007/10/02)
Inorganic solid bases give rise to α-elimination reactions of NsONHCO2Et under easy and mild conditions without catalyst or ultrasounds. For several kinds of substrates, a comparison of yields and reaction times with previous methods is presented.
CAN (ETHOXYCARBONYL)NITRENE SELECTIVITY BE CONTROLLED BY MICELLAR PSEUDOPHASE?
Bertolaccini, Riccardo,Cerichelli, Giorgio,Loreto, M. Antonietta,Pellacani, Lucio,Tardella, Paolo A.
, p. 587 - 588 (2007/10/02)
The effect of cationic surfactants in the reaction of cyclohexene and (ethoxycarbonyl)nitrene has been studied.When the counter-ion of the surfactant was bromide, the products of bromination of cyclohexene or those requiring the intermediacy of nitrene were observed.The latter were the only products if nitrate was the counter-ion of the surfactant, using N-oxy>urethan, even without added base.
THE ELECTROCHEMICAL REDUCTION OF N-FLUOROETHANS IN ACETONITRILE. THE GENERATION OF CARBETHOXYNITRENE
Lessard, Jean,Berube, Denis
, p. 768 - 777 (2007/10/02)
The electrochemical reduction of N-fluoro-N-methylurethan (1a) and N-fluorourethan (2a) in acetonitrile generates the amide anion and fluoride ion.Both the fluoride and the amide react with the starting N-fluoroamide either as bases or as nucleophiles.Many products are formed and the coulometric results are low (0.5 to 0.7 F/mol).In the case of NFU (2a), abstraction of the proton on nitrogen both by the urethan anion and the fluoride anion generates the conjugate base EtOCOF (7) which immediately undergoes α-elimination of the fluoride ion to give carbethoxynitrene (11).This nitrene was generated also by treating NFU (2a) with a base such as triethylamine of lithium hydride.The α-elimination of F1- from EtOCOF is much easier than α-elimination of Cl1- from EtOCOCl.
Azimines VI: 1-Alkoxycarbonyl-2,3-dialkyl- and 2,3-diarylazimines
Leuenberger, Christian,Hoesch, Lienhard,Dreiding, Andre S.
, p. 217 - 228 (2007/10/02)
Alkoxycarbonyl-nitrenes 2 - generated in situ by α-elimination from N-carbamates 4 - were reacted with six aliphatic and aromatic azo compounds to yield 1-alkoxycarbonyl-azimines 11 (R' = Alkyl).Thus, (2Z)- or (2E)-1-alkoxycar
