Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reactions of Aryl Organometallic Reagents with Isomers of Phthalonitriles: Triaryl Diketimines and Diketones

  • Lee, Woo-Young (Department of Chemistry, Seoul National University) ;
  • Kim, Young-Soo (Department of Chemistry, Seoul National University) ;
  • Sim, Won-Bo (Department of Chemistry, Seoul National University) ;
  • Park, Chang-Hee (Department of Chemistry, Seoul National University) ;
  • Ahn, Yoon-Mo (Department of Chemistry, Seoul National University) ;
  • Park, Oee-Sook (Department of Chemistry, Chungbuk National University)
  • Published : 1986.10.20
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Abstract

Synthesis and hydrolysis of aromatic diketimines of triaryl type were investigated by the action of aryl organometallics on the three isomers of phthalonitrile. The reactions of organometallic reagents, prepared from bromobenzene, o-bromotoluene and o-bromoanisol, with iso- and terephthalonitrile proceeded in normal way. Decomposition of the addition complex with dry ammonia, methanol or water gave six diketimines, which could be hydrolysed to the corresponding diketones. Reactions of phthalonitrile with the organometallic reagent were different from the other isomers, so that the decomposition and hydrolysis of the addition complex did not give diimines and the corresponding aromatic diketones.

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