Synthesis and reactivity of ferrocenyl-substituted allylamine derivatives
Résumé
[(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.