Controlled friedel-crafts acylation of 3, 6-disubstituted-9H-carbazole

Ting Yu Lee, Ming Che Yeh, Ling Chueh Chang, Chi Wi Ong, Che Yu Lin, Jui-Hsien Huang

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Abstract

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-9H-carbazoles (2) by the direct Friedel-Crafts acylation of 3, 6-di-tert-butyl-9H-carbazole (1) is described. During the reaction, the dealkylation also occurred, and 1, 8-diacetyl-3-tert- butyl-9H-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.

Original languageEnglish
Pages (from-to)773-778
Number of pages6
JournalJournal of the Chinese Chemical Society
Volume60
Issue number7
DOIs
Publication statusPublished - 2013 Oct 21

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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