53697-04-4Relevant academic research and scientific papers
Imines and Derivatives. Part 24. Nitrone Synthesis by Imine Oxidation using either a Peroxyacid or Dimethyldioxirane
Boyd, Derek R.,Coulter, Peter B.,McGuckin, M. Rosaleen,Sharma, Narain D.,Jennings, W. Brian,Wilson, Valerie E.
, p. 301 - 306 (2007/10/02)
The oxidation of N-alkyl imines by m-chloroperoxybenzoic acid to yield nitrones was facilitated by (i) the presence of C-aryl substituents, (ii) steric inhibition of attack at the imino C-atom, (iii) electron donating para-substituents on the C-aryl substituent, (iv) non-hydroxylic solvents, (v) optimal conjugation between C-aryl substituents and the imino group, and (vi) less bulky N-alkyl groups. The oxidation of N-alkyl imines by dimethyldioxirane (DMD) in dichloromethane-acetone solution yielded nitrones without evidence of oxaziridine formation.The yields of isolated nitrones were higher for C,C-diaryl imines and for imines bearing less bulky N-alkyl substituents.N-H substituted ketimines were found to yield oximes after reaction with dimethyldioxirane.
NORMAL, ABNORMAL AND PSEUDO-ABNORMAL REACTION PATHWAYS FOR THE IMINE-PEROXYACID REACTION
Boyd, Derek R.,Coulter, Peter B.,Sharma, Narain D.,Jennings, Brian W.,Wilson, Valerie E.
, p. 1673 - 1676 (2007/10/02)
Steric and mesomeric effects have a marked influence upon the formation of oxaziridine (normal pathway) or nitrone (abnormal pathway) products from the imine-peroxyacid reaction; n.m.r. studies of the thermal isomerization of oxaziridines to nitrones prov
