Fused‐ s ‐triazino heterocycles. XI. Displacement reactions of 7,9‐dichloro‐2,5‐bis(trichloromethyl)‐1,3,4,6,9b‐pentaazaphenalene | Zendy

Shaw John T. | Zendy; Rapple Rodney S. | Zendy; Hicks John C. | Zendy; Vossers John T. | Zendy

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Fused‐ s ‐triazino heterocycles. XI. Displacement reactions of 7,9‐dichloro‐2,5‐bis(trichloromethyl)‐1,3,4,6,9b‐pentaazaphenalene

Author(s) -

Shaw John T.,

Rapple Rodney S.,

Hicks John C.,

Vossers John T.

Publication year - 1984

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570210232

Subject(s) - chemistry , chlorine , chlorine atom , nucleophile , medicinal chemistry , substitution reaction , displacement (psychology) , nucleophilic substitution , organic chemistry , catalysis , psychology , psychotherapist

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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