80167-06-2Relevant academic research and scientific papers
Regioselective nitration of deactivated mono-substituted benzenes using acyl nitrates over reusable acidic zeolite catalysts
Smith, Keith,Ajarim, Mansour D.,El-Hiti, Gamal A.
, p. 270 - 278 (2010)
Nitration of benzonitrile was investigated using a nitric acid/acid anhydride/zeolite catalyst system under different reaction conditions. Trifluoroacetic and chloroacetic anhydrides were found to be the most active among the anhydrides tried. Also, zeolites Hβ and Fe3+β (Si/ Al = 12.5) were found to be the most active catalysts. For example, nitration of benzonitrile with trifluoroacetyl nitrate under reflux conditions in dichloromethane gave 3- and 4-nitrobenzonitriles in quantitative yield, of which the para-isomer represented 24-28%. The yield of para-isomer was improved to 33% when passivated Hβ was used under similar reaction conditions. This is easily the most para-selective nitration of benzonitrile ever recorded. Also, no ortho-isomer was formed under the conditions tried. The zeolite can be easily recovered, regenerated by heating and reused up to six times to give results similar to those obtained with a fresh sample of the catalyst. The nitration system was applied successfully to a range of deactivated mono-substituted benzenes to give para-isomers in significantly higher proportions than in the corresponding traditional nitration reactions.
Nitration of deactivated aromatic compounds via mechanochemical reaction
Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
supporting information, (2021/05/05)
A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.
Ozone-mediated Nitration of Aromatic Ketones and Related Compounds with Nitrogen Dioxide
Suzuki, Hitomi,Murashima, Takashi
, p. 903 - 908 (2007/10/02)
Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give ortho- and meta-nitro derivatives as the principal products, the former usually being predominant (ortho:meta = 1.1-3.8:1.0).No attack was observed on the alkyl side chains.
THE NITRATION OF PIVALOPHENONE WITH NITRONIUM TETRAFLUOROBORATE IN SULFOLANE
Zieger, Herman E.,Lee, Brendan
, p. 2707 - 2714 (2007/10/02)
The nitration of pivalophenone (2,2-dimethyl-1-phenylpropan-1-one) with NO2BF4 gives o-, m-, and p-nitropivalophenones in the percentage ratio of 26:45:29.Competition experiments showed that pivalophenone is ten to twenty times less reactive than benzene
The Nitration of Pivalophenone
Barker, Steven D.,Norris, Robert K.,Randles, David
, p. 1875 - 1878 (2007/10/02)
The nitration of pivalophenone (2,2-dimethyl-1-phenylpropan-1-one), which is the first reported electrophilic substitution on that substrate, gives o-, m- and p-nitropivalophenones in the percentage ratio 30:44:26.This anomalous product distribution, whic
