Editing Nitration (section)

===Ipso nitration===
With aryl chlorides, [[triflate]]s and nonaflates, [[Arene substitution pattern#Ipso.2C meso.2C and peri substitution|ipso]] nitration may also take place.<ref>{{Cite journal| doi = 10.1002/anie.200906940| pmid = 20146295| year = 2010| last1 = Prakash | first1 = G.| last2 = Mathew | first2 = T.| title = Ipso-Nitration of Arenes| volume = 49| issue = 10| pages = 1726–1728| journal = Angewandte Chemie International Edition in English }}</ref> The phrase '''ipso nitration''' was first used by Perrin and Skinner in 1971, in an investigation into chloroanisole nitration.<ref>{{Cite journal| doi = 10.1021/ja00743a015| title = Directive effects in electrophilic aromatic substitution ("ipso factors"). Nitration of haloanisoles| year = 1971| last1 = Perrin | first1 = C. L.| last2 = Skinner | first2 = G. A.| journal = Journal of the American Chemical Society| volume = 93| issue = 14| pages = 3389 }}</ref> In one protocol, 4-chloro-''n''-butylbenzene is reacted with [[sodium nitrite]] in [[tert-butanol|''t''-butanol]] in the presence of  0.5&nbsp;mol% [[Tris(dibenzylideneacetone)dipalladium(0)|Pd<sub>2</sub>(dba)<sub>3</sub>]], a biarylphosphine ligand and a [[phase-transfer catalyst]] to provide 4-nitro-''n''-butylbenzene.<ref>{{Cite journal| doi = 10.1021/ja905768k| pmid = 19737014| year = 2009| last1 = Fors | first1 = B.| last2 = Buchwald | first2 = S.| title = Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics| journal = Journal of the American Chemical Society| volume = 131| issue = 36| pages = 12898–12899| pmc = 2773681}}</ref>