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Controlled Friedel‐Crafts Acylation of 3,6‐Disubstituted‐ 9H ‐carbazole
Author(s) -
Lee TingYu,
Yeh MingChe,
Chang LingChueh,
Ong ChiWi,
Lin CheYu,
Huang JuiHsien
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201200575
Subject(s) - chemistry , friedel–crafts reaction , carbazole , acylation , alkylation , steric effects , medicinal chemistry , diacetyl , organic chemistry , catalysis
1,8‐Dicarbonylcarbazoles are important starting materials for various applications, especially for pincer‐type ligands. The convenient synthesis of a series of 1,8‐diacyl‐3,6‐di‐ tert ‐butyl‐9 H ‐carbazoles ( 2 ) by the direct Friedel‐Crafts acylation of 3,6‐di‐ tert ‐butyl‐9 H ‐carbazole ( 1 ) is described. During the reaction, the dealkylation also occurred, and 1,8‐diacetyl‐3‐ tert ‐butyl‐9 H ‐carbazole ( 4 ) was isolated as well as characterized by an X‐ray diffraction analysis. In addition, the steric bulkiness of the acyl chlorides strongly affects the yields of 1,8‐diacylation of 1 .