88073-07-8Relevant academic research and scientific papers
Reactivity of N-Phenacyloxycarbamates and Related Systems in the Presence of Bases: Study of a New Anionic Rearrangement
Consonni, Piero,Favara, Duccio,Omodei-Sale, Amedeo,Bartolini, Giuseppe,Ricci, Alfredo
, p. 967 - 974 (2007/10/02)
N-Phenacyloxycarbamates and other systems containing a CH2-O-N= framework, in the presence of bases, undergo a CH2-O-N= -> CH(OH)-N= rearrangement.The mechanism of this reaction has been studied kinetically and through crossover and capture experiments.The bulk of the data favours an intermolecular ionic mechanism which occurs by removal of a proton from the methylene group in the rate-determining step, followed by interaction between a glyoxal molecule and a carbamate anion in the fast step of the reaction.
