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Report | Regular issue | Vol 23, No. 2, 1985, pp.357-363
Published online, 1st January, 1970
DOI: 10.3987/R-1985-02-0357
Metalation of 2-Trifluoromethylphenothiazine: Synthesis and Reactions of Trimethylsilyl Derivatives

Arne Svensson and Arnold R. Martin*

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.


Dimetalation of 2-trifluoromethylphenothiazine followed by reaction with electrophiles such as carbon dioxide, DMF, hexachloroethane and 1,2-dibromoethane gives 1-substituted 2-trifluoromethylphenothiazines with only traces of the 9-substituted products being formed. Reaction of 1,10-dilithio-2-trifluoromethylphenothiazine with an excess of trimethylysilyl chloride gave a mixture of 2-trifluoromethyl-10-trimethylsilylphenothiazine and 2-trifluoromethyl-1,10-di(trimethylsilyl)phenothiazine. The 10-trimethylsilyl- and 2-trifluoromethyl-1,10-di(trimethylsilyi)phenothiazines were prepared from 10-lithio- and 1-lithio-2-trifluoromethylphenothiazine, respectively. The basis for the unusual stability of 1,10-dilithio-2-trifluoromethylphenothiazine is discussed.