4098-70-8Relevant academic research and scientific papers
CHROMIUM(II) PROMOTED ADDITION OF N-CHLOROCARBAMATES TO ALKENES
Gerber, J. P.,Goosen, A.,McCleland, C. W.
, p. 3037 - 3051 (2007/10/02)
Ethyl N-chloro-N-methylcarbamate has been shown to produce adducts with some alkenes.The role of the chromium(II) species in the reaction is discussed.
BORON TRIFLUORIDE PROMOTED REACTIONS OF N-HALOELECTROPHILES WITH ALKENES
Heasley, Gene E.,Janes, J. Mark,Stark, Stephen R.,Robinson, Brian L.,Heasley, Victor L.,Shellhamer, Dale F.
, p. 1811 - 1814 (2007/10/02)
N-Haloelectrophiles react with alkenes in the presence of boron trifluoride etherate to give halofluorides and N-halo adducts.
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.
The photochemical addition of N-haloamides to olefins: the influence of various factors on the competition between 1,2-addition and hydrogen abstraction
Lessard, Jean,Mondon, Martine,Touchard, Daniel
, p. 431 - 450 (2007/10/02)
In the photodecomposition of N-haloamides (ZCONRX) in the presence of olefins, the 1,2-addition chain competes with the hydrogen abstraction chain(s) leading to the parent amide (the quantum yields for these processes are greater than unity).The following factors were shown to have an influence on this competition as measured by the yield of 1,2-addition and the yield of parent amide in methylene chloride solutions: (i) the N-halogen (higher yields of addition with X=Cl than with X=Br); (ii) the electronegativity of Z (increase of the yield of addition as the electronegativity of Z increases); (iii) the temperature (higher yields of addition at lower temperatures, and at -70 degC, better yields of addition (>90percent, R=H) for X=Br than for X=Cl); and (iv) the size of R (dramatic decrease of the yield of 1,2-addition in going from R=H to R=CH3).Surprisingly, the presence of a scavenger for HX had no influence on the yield of 1,2-addition.Both the size and electronegativity of Z had an effect on the stereochemistry of 1,2-addition to cyclohexene.High yields of addition to a variety of olefins were obtained with N-chloroamides such as ClCH2CONHCl, C2H5OCONHCl, CF3CONHCl.Their addition to enol ethers at -70 degC led to the synthesis of α-amido acetals or ketals (aldehydes or ketones) and to an α-amido glycoside in good yields.
