83687-69-8Relevant academic research and scientific papers
Role of the macrocyclic polyether in the synthesis of N-alkylcarbamate ester from primary amines, CO2 and alkyl halides in the presence of crown-ethers
Aresta,Quaranta
, p. 1515 - 1530 (1992)
Primary amines, RNH2 1, and CO2 easily afford monoalkylammonium N-alkylcarbamates, [RNH3][O2CNHR] 2, that have been reacted with alkyl halides, R'X, in the presence of crown-ethers to give organic carbamates in good yield. We report here the synthesis and spectroscopic characterization of some alkylammonium carbamates 2, where R - benzyl 2a, allyl 2b, ter-butyl 2c, cyclohexyl 2d, and discuss their stability in solution and the conditions in which they can react with alkyl halides to give organic carbamates, RNHC(O)OR'. The role played by the macrocyclic ligand in modifying the reactivity of monoalkylammonium carbamates 2 towards R'X has been rationalized and the influence of parameters such as solvent, temperature and CO2 pressure on the yield and selectivity of the process leading to organic carbamates has been also settled.
The reaction of amines with benzyl halides under CO2 atmosphere
Shi,Shen
, p. 3357 - 3365 (2007/10/03)
To find a useful, practical, and ecologically safer way to synthesize protected amines, the reactions of amines with benzyl halides under CO2 atmosphere were systematically examined. For primary amines, the CO2-inserted products were obtained in higher yields in the presence of DBU as a base, under a high pressure of CO2, and in a low-polarity solvent (toluene/hexane 1:1). Secondary amines gave only low yields of CO2-inserted products.
