M. D. Dutov, S. A. Shevelev, V. N. Koshelev, D. R. Aleksanyan, O. V. Serushkina, O. D. Neverova, E. V. Kolvina, E. S. Bobrov, “Dual reactivity of 1-chloro- and 1-bromo-3,5-dinitrobenzenes in aromatic nucleophilic substitution”, Mendeleev Commun., 2017, Volume 27, Issue 2,Pages <nobr>160

This article is cited in 3 papers

Communications

Dual reactivity of 1-chloro- and 1-bromo-3,5-dinitrobenzenes in aromatic nucleophilic substitution

M. D. Dutov^a, S. A. Shevelev^a, V. N. Koshelev^b, D. R. Aleksanyan^b, O. V. Serushkina^a, O. D. Neverova^a, E. V. Kolvina^b, E. S. Bobrov^c

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b National University of Oil and Gas ‘Gubkin University’, Moscow, Russian Federation
^c D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: Aromatic nucleophilic substitution reactions in 1-halo-3,5-dinitrobenzenes (where the halogen is bromine or chlorine) can occur with replacement of either a nitro group or a halogen atom, depending on the nature of anionic nucleophile Nu^– as a Lewis base (hard, soft or intermediate), as well as on the polarity of the dipolar aprotic solvent.

Language: English

DOI: 10.1016/j.mencom.2017.03.018