Fused-s-triazino heterocycles. XI. Displacement reactions of 7,9-dichloro-2,5-bis(trichloromethyl)-1,3,4,6,9b-pentaazaphenalene |
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| Authors: | John T Shaw Rodney S Rapple John C Hicks John T Vossers |
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| Institution: | 1. Department of Chemistry, Grove City College, Grove City, Pennsylvania 16127;2. Department of Chemistry, Grove City College, Grove City, Pennsylvania 16127
Petroleum Research Fund Undergraduate Research Participant. |
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| Abstract: | The preparation of 7,9-dichloro-2,5-bis(trichloromethyl)-1,3,4,6,9b-pentaazaphenalene ( 1e ) by the chlorination of 2-trichloromethyl-5-methyl-1,3,4,6,9b-pentaazaphenalene ( 1a ) using molecular chlorine is described. Displacement of one or both trichloromethyl groups of 1e by a variety of nucleophiles led to the corresponding 7,9-dichloro-2,5-bis-substituted or 7,9-dichloro mixed 2,5-disubstituted derivatives. The reaction of 1a with N-chlorosuccinimide proved not to be a useful route to 1e but instead led primarily to substitution of positions 7 and/or 9 by chlorine. |
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