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Synthesis of New Sterically Hindered Anilines
Author(s) -
Steele Barry R.,
Georgakopoulos Spyros,
MichaScrettas Maria,
Screttas Constantinos G.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700233
Subject(s) - chemistry , steric effects , superbase , ring (chemistry) , alkylation , primary (astronomy) , ethylene , medicinal chemistry , organic chemistry , stereochemistry , catalysis , physics , astronomy
Ring‐alkylated primary, secondary and tertiary anilines have been ethylated with ethylene at benzylic positions in a simple and inexpensive one‐pot procedure which is mediated bythe use of the superbase system n BuLi/LiK(OCH 2 CH 2 NMe 2 ) 2 in the presence of Mg(OCH 2 CH 2 OEt) 2 . Primary and secondary anilines are ethylated readily at ortho ‐benzylic positions but with difficulty or not at all at other positions. Tertiaryanilines are ethylated at all positions. Mono‐ or diethylation occurs depending on the steric constraints present.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)