54357-08-3Relevant academic research and scientific papers
Nitration of Reactive Aromatics via Elelctron Transfer. V. On the Reaction between Nitrogen Dioxide and the Radical Cation Hexafluorophosphates of Some Methyl-substituted Naphthalenes
Eberson, Lennart,Radner, Finn
, p. 71 - 78 (2007/10/02)
The coupling reactions of series of methylnaphthalene radical cation hexafluorophosphates with nitrogen dioxide were studied in dichloromethane at low temperatures.Yields of nitro derivatives were generally higher with the β-methyl than with the α-methyl-substituted naphthalenes and the isomer distributions were different from those obtained in electrophilic aromatic nitration and nitrous acid catalyzed nitration.This confirm an earlier suggestion that the coupling reaction is not an elementary step of either nitration process.The high regioselectivity of the coupling reation can only partly be correlated with UHF spin densities.Pyrene+. hexafluorophosphate does not yield nitropyrenes upon treatment with nitrogen dioxide.This confirm earlier suggestions that only radical cations of aromatics with Eo values >= 1.7 V will take part in a successful (exergonic) coupling reaction with nitrogen dioxide.
