Synthesis of New Sterically Hindered Anilines

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 nBuLi/LiK(OCH2CH2NMe2)2in the presence of Mg(OCH2CH2OEt)2. Primary and secondary anilines...

Full description

Saved in:
Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-07, Vol.2007 (19), p.3091-3094
Main Authors: Steele, Barry R., Georgakopoulos, Spyros, Micha-Screttas, Maria, Screttas, Constantinos G.
Format: Article
Language:English
Subjects:
Alkylation
Amines
Carbanions
Metalation
Steric Hindrance
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 nBuLi/LiK(OCH2CH2NMe2)2in the presence of Mg(OCH2CH2OEt)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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700233