134450-66-1Relevant articles and documents
Succinimidylation and nitration of aromatic compounds by photolysis with N-nitrosuccinimide
Calvert, Jane,Eberson, Lennart,Hartshorn, Michael P.,Svensson, Jan O.
, p. 645 - 652 (2007/10/02)
N-Nitrosuccinimide (S-NO2) engages in weak charge transfer complexes with aromatic compounds (ArH).Upon photolysis with light of λ > 345 nm in dichloromethane, electron transfer within the charge transfer complex leads to the triad -NO2>from which products of eventual succinimidylation and/or nitration develop by initial attack of succinimide anion upon the radical cation.Photolysis in the presence of trifluoroacetic acid (0.4 mol dm-3) causes inactivation of S- by protonation, making EPR detection of ArH-radical cations or radicals cations formed by its further transformations possible.In acetonitrile, trifluoroacetic acid is too weak effectively to protonate S-, whereas addition of stronger acids again leads to the development of EPR spectra of ArH-radical cation in the case of 9,10-dimethylanthracene, the intensity increasing with decreasing pK of the acid.An X-ray crystal structure is reported for N-nitrosuccinimide.