Synthesis and Reactivity of Ferrocenyl-Substituted Allylamine Derivatives

Abstract

[(2-Ferrocenylvinyl)methyl]dimethylamine (2) was obtained in good yields and with perfect regio- and stereoselectivity by reaction of dimethylmethylideneammonium salts with vinylferrocene. After methylation of amine 2, [(2-ferrocenylvinyl)methyl]trimethylammonium iodide (4) was obtained in high yields and used to transfer the ferrocene-containing allyl group to various amines. By controlling reaction conditions, various linear and branched ferrocenyl-substituted allylamines could be obtained with good yields and selectivities. When anilines were used as substrates against ammonium salt 4, compounds originating from Friedel–Crafts reactions were also obtained, with complete regioselectivity towards the para position.