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Paper | Regular issue | Vol 53, No. 2, 2000, pp.373-380
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8787
Investigation on the Reaction of 2-Chloro-10H -phenothiazine under Aryne Forming Conditions

Anlai Wang, Hongming Zhang, and Edward R. Biehl*

*Chemistry Department, Southern Methodist University, Dallas, Texas 75275, U.S.A.


The reaction of 2-chloro-10H -phenothiazine with a variety of arylacetonitriles and α-cyano-o-tolunitrile in the presence of LTMP gave 2-arylmethyl-10H -phenothiathiazine-1-carbonitriles and 13-amino-14H -naphtho[2,3-b]phenothiazine-8-carbonitrile, respectively. Interestingly, LTMP effectively trapped 10-lithio-1,2-didehydrophenothiazine to give 2-(2,2,6,6-tetramethylpiperidin-1-yl)-10H -phenothiazine.