75755-31-6Relevant articles and documents
NUCLEOPHILIC HETEROAROMATIC SUBSTITUTIONS. XXXIX. THE REACTION OF α- AND γ-- AND α- AND γ--7-NITROQUINOLINE WITH PIPERIDINE IN BENZONITRILE: BASE CATALYSIS AND O vs S REACTIVITY
Cidda, Claudio,Sleiter, Giancarlo
, p. 155 - 162 (2007/10/02)
The reactivity of the title compounds with piperidine has been examined.Product analysis showed that substitution is accompanied by other processes, the extent of which depends on the reactivity of the substrates towards nucleophilic substitution and is greatest in the case of the γ-arylthio derivative, which does not undergo substitution at all.Accordingly, a kinetic analysis of the reaction could be performed only for the two aryloxy and the α-arylthio derivatives.Second-order rate coefficients for the reactions of the α-substituted quinolines were found to be independent of amine concentration and the α-aryloxy derivative was found to be only ca 4 times as reactive as the α-arylthio compound.In contrast, the reaction of the γ-aryloxy derivative followed third-order kinetics and turned out to be base-catalysed because it was accelerated by added quinuclidine.The reaction mechanisms are discussed in the light of these observations and other, previously reported, facts.