76016-34-7Relevant articles and documents
Vicarious nucleophilic substitution of hydrogen proceeding via heterocyclic ring opening
Makosza, Mieczyslaw,Sypniewski, Michal,Glinka, Tomasz
, p. 3189 - 3194 (1996)
Carbanions of five-membered S-heterocycles react with nitroarenes via the ring-opening VNS reaction or oxidative nucleophilic substitution of hydrogen. The reaction course is affected by rigidity of the ring.
Experiments on the Chaperon effect in the nitration of aromatics
Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
, p. 952 - 958 (2007/10/03)
A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.
Ring-Chain Tautomerism in Anions Derived from Substituted (Arylideneamino)toluenes and (Arylideneamino)oxindoles
Goetz, Frederick J.,Hirsch, Jerry A.,Augustine, Robert L.
, p. 2468 - 2472 (2007/10/02)
Intramolecular nucleophilic attack by carbon and nitrogen anions on imine and enone double bonds, respectively, has been investigated as a synthetic route to fused five-membered azacycles.In both (arylideneamino)toluenes and (arylideneamino)oxindoles, cyc