Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. Part 10. Reactions of s-alkyl primary amines with pyryliums
作者:Alan R. Katritzky、Jorge Marquet、Jeremy M. Lloyd、James G. Keay
DOI:10.1039/p29830001435
日期:——
α-phenylbenzylamine forms the corresponding carbonium ions which may be trapped by nucleophiles. Isolated 1-cycloalkylbenzoquinoliniums (2) solvolyse but the SN1 mechanism (for five-, six-, and seven-membered rings): for the cyclobutyl case an SN2 reaction is also found.
2,4,6-三苯基吡啶与仲烷基胺可制得可分离的吡啶鎓(吡啶鎓被亲核试剂取代为S N 2并消除为烯烃)。与1-苯基乙胺和α-苯基苄基胺形成的2,4,6-三苯基吡啶鎓形成相应的碳离子,这些碳离子可能被亲核试剂捕获。分离的1-环烷基苯并喹啉鎓盐(2)溶剂分解但具有S N 1机理(对于五元,六元和七元环):对于环丁基,还会发现S N 2反应。