Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems 英文参考文献.docVIP

Molecules 2008, 13, 1345-1352; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Article Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems Steven C. Farmer* and Seth H. Berg Department of Chemistry, Sonoma State University, 1801 East Cotati Avenue, Rohnert Park, California 94928, USA * Author to whom correspondence should be addressed; E-mail: farmers@; Phone: +1-(707) 664-3728 Received: 1 June 2008; in revised form: 10 June 2008 / Accepted: 10 June 2008 / Publshed: 12 June 2008 Abstract: 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-ethyl- phenothiazine, 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. Keywords: Phenothiazine; Desulfurization; Sulfoxides; Sulfones Introduction Past research has focused on the sulfur extrusion reactions of heterocycles [1], mainly because of their applications in the desulfurization of fossil fuels [2]. Some examples of the ring contraction of phenothiazine (1) to make carbazole (2) and of 10-ethylphenothiazine (3) to make 9-ethylcarbazole (4) [3-5] have been reported. However, to our knowledge there have been no reported attempts at causing a similar desulfurization from the phenothiazine-5-oxide (5), phenothiazine-5,5-dioxide (6), 10-ethyl-  Molecules 2008, 13 1346 phenothiazine-5-oxide (7) and 10-ethylphenothiazine-5,5-dioxide (8) as S-oxidized derivatives of this ring system. An efficient method for these ring contractions could prove useful because mos