Ring contracting sulfur extrusion from oxidized phenothiazine ring systems.
Lithium, used in conjunction with sodium metal, produces a high yield of carbazole when reacted with phenothiazine-5-oxide or phenothiazine-5,5-dioxide. A high yield of 9-ethylcarbazole is also produced when these reagents react with 10-ethylphenothiazine, 10-ethylphenothiazine-5-oxide, and 10-ethylphenothiazine-5,5-dioxide. Degassed Raney nickel produces carbazole in high yield when reacted with phenothiazine and phenothiazine-5-oxide. A moderate yield of 9-ethylcarbazole is produced when n-butyllithium is reacted with 10-ethylphenothiazine-5-oxide.
Farmer
Steven C
SC
Department of Chemistry, Sonoma State University, 1801 East Cotati Avenue, Rohnert Park, California 94928, USA. farmers@sonoma.edu
Berg
Seth H
SH
D002227:Carbazoles / Q000138:chemical synthesis; D008094:Lithium; D009532:Nickel; D010640:Phenothiazines / Q000737:chemistry*; D013455:Sulfur
D002227:Carbazoles; D010640:Phenothiazines; D013455:Sulfur; D009532:Nickel; D008094:Lithium; C031637:phenothiazine