Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems

doi:10.3390/molecules13061345

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Molecules 2008, 13(6), 1345-1352; doi:10.3390/molecules13061345

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.

Received: 1 June 2008; in revised form: 10 June 2008 / Accepted: 10 June 2008 / Published: 12 June 2008

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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-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.

Keywords: Phenothiazine; Desulfurization; Sulfoxides; Sulfones

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Cite This Article

MDPI and ACS Style

Farmer, S.C.; Berg, S.H. Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems. Molecules 2008, 13, 1345-1352.

AMA Style

Farmer SC, Berg SH. Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems. Molecules. 2008; 13(6):1345-1352.

Chicago/Turabian Style

Farmer, Steven C.; Berg, Seth H. 2008. "Ring Contracting Sulfur Extrusion from Oxidized Phenothiazine Ring Systems." Molecules 13, no. 6: 1345-1352.

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