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The chemistry of carbazole. VI. On the formation of N ‐ethylcarbazoles in the cadogan reaction
Author(s) -
Tsunashima Yutaka,
Kuroki Masatane
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180217
Subject(s) - chemistry , nitrene , phosphoramidate , carbazole , medicinal chemistry , organic chemistry , polymer chemistry , stereochemistry , catalysis
Reaction of 2′,6‐dimethyl‐2‐nitrobiphenyl with triethyl phosphite gave 4,5‐dimethyl‐9‐ethylcarbazole besides 4,5‐dimethylcarbazole. In this reaction, 4,5‐dimethylcarbazole was ethylated by triethyl N ‐(2′,6‐dimethybiphenyl‐2‐yl)phosphorimidate and diethyl N ‐(2′,6‐dimethylbiphenyl‐2‐yl)phosphoramidate, which arose from a nitrene‐intermediate and triethyl phosphite. Analogous ethylations of carbazole with other phosphorimidate and phosphoramidates were investigated.