26107-15-3Relevant academic research and scientific papers
AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES: EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES
Atkinson, Robert S.,Grimshire, Michael J.,Kelly, Brian J.
, p. 2875 - 2886 (1989)
Oxidation of 3-aminoquinazolones e.g. (22) with lead tetra-acetate at -20 deg C gives N-acetoxyaminoquinazolones e.g. (23) which are stable in solution at this temperature.These N-acetoxyaminoquinazolones function as inter- and intramolecular aziridinating agents for alkenes and appear to be playing the role previously ascribed to the corresponding N-nitrenes.An analogous N-acetoxyaminophthalimide intermediate (31) is implicated in the lead tetra-acetate oxidation of N-aminophthalimide (4).
Sodium-iodoxybenzoate mediated highly chemoselective aziridination of olefins
Bakthavachalam, Ananthan,Chuang, Hui-Chun,Yan, Tu-Hsin
, p. 5884 - 5894 (2015/03/30)
Herein we utilized, for the first time, sodium 2-iodoxybenzoate as a highly specific oxidant for PhthNH2 to create a highly chemoselective aziridination reagent. This method efficiently effects aziridination of electron-rich, electron-deficient, allylic alcohol and alkenyl bromide C=C bonds in good to excellent yields. Inter and intramolecular chemoselectivity was demonstrated between electron-rich and electron-deficient alkenes by using this efficient and metal free protocol.
Evidence for Phthalimidonitrene as a Common Intermediate in Several Extrusion Reactions
Atkinson, Robert S.,Jones, David W.,Kelly, Brian J.
, p. 1344 - 1346 (2007/10/02)
A common intermediate, presumably phthalimidonitrene 1, is generated in the thermolysis of the aziridinobenzofurans 3 (R = Ac, CO2Me, Bz, COBut and CN) as well as the sulphimide 4, and the azabenzonorbornadiene 5.The transfer of 1 shown in Scheme 1 is zero order in 2-acetylbenzofuran providing further evidence against a concerted bimolecular mechanism 10 for 'nitrene' transfer.
