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Synthesis and Reactivity of Ferrocenyl‐Substituted Allylamine Derivatives
Author(s) -
Bouchene Rafika,
Daran JeanClaude,
Bouacida Sofiane,
Manoury Eric
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600860
Subject(s) - chemistry , allylamine , regioselectivity , dimethylamine , reactivity (psychology) , ferrocene , methyl iodide , amine gas treating , stereoselectivity , organic chemistry , iodide , medicinal chemistry , salt (chemistry) , catalysis , polyelectrolyte , medicine , polymer , alternative medicine , electrode , pathology , electrochemistry
[(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.