NITRATION OF STRONGLY DEACTIVATED AROMATICS WITH SUPERACIDIC MIXED NITRIC-TRIFLATOBORIC ACID (HNO3 2CF(3)SO(3)H-B(O3SCF3)(3))/

Citation
Ga. Olah et al., NITRATION OF STRONGLY DEACTIVATED AROMATICS WITH SUPERACIDIC MIXED NITRIC-TRIFLATOBORIC ACID (HNO3 2CF(3)SO(3)H-B(O3SCF3)(3))/, Journal of organic chemistry, 60(22), 1995, pp. 7348-7350
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
60
Issue
22
Year of publication
1995
Pages
7348 - 7350
Database
ISI
SICI code
0022-3263(1995)60:22<7348:NOSDAW>2.0.ZU;2-3
Abstract
The nitration of various deactivated arenes (including methanesulfonyl -, nitro-, and polyhalobenzenes) was carried out in good yield with mi xed nitric-triflatoboric superacid. For example pentafluorobenzene gav e pentafluoronitrobenzene in 99% yield, nitrobenzene to m-dinitrobenze ne in 92% selectivity with 85% overall yield, and methyl phenyl sulfon e gave only the m-nitro isomer in 78% isolated yield. Thus the new nit rating system gives high regioselectivity and yields under generally m ild reaction conditions. The reagent system is compatible with many fu nctional groups of arenes.