Base-mediated Reaction of Quaternary Ammonium Salts with Nitroarenes - Their Useful Functionalization via Vicarious Nucleophilic Substitution (VNS)

Ammonium ylides generated from ammonium salt 1a-e with a base react with derivatives of 3-nitropyridine 2a-c and 2-nitrothiophene (3) to form products of vicarious nucleophilic substitution (VNS) 7, 8, or 9 respectively. The products of VNS 10, 11, or 12 are also produced from the corresponding ammonium salts, a base and 4-chloro-nitrobenzene (4), nitrobenzene (5), or 1-nitronaphthalene (6), respectively. In a few products, an exchange of alkoxy group 7c or substitution of chlorine by alkoxyl 8a,b occured.