Premium
Overcrowded 5,10,15‐Trisubstituted Derivatives: Synthesis of 5,10,15‐Tri(fluorenylidene)truxene
Author(s) -
Ruiz Marta,
GómezLor Berta,
Santos Amelia,
Echavarren Antonio M.
Publication year - 2004
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.200300632
Subject(s) - chemistry , isomerization , steric effects , aryl , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , alkyl
Sterically crowded 5,10,15‐triarylated truxenes are obtained by reaction of truxenetrione with aryllithium compounds (aryl = 1‐naphthyl, 2‐naphthyl, 9‐phenanthryl, 9‐anthracenyl), followed by reduction of the tertiary alcohols with Et 3 SiH and BF 3 . Base‐catalyzed isomerization of the anti derivatives provides syn ‐5,10,15‐triarylated derivatives, with the exception of the 9‐anthracenyl that could not be isomerized. Overcrowded 5,10,15‐tri(fluorenylidene)truxene was also synthesized starting form the addition of fluorenyllithium to truxenetrione. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)