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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 7, Number 5
May 20, 1986 

Reactions of Aryl Organometallic Reagents with Isomers of Phthalonitiles: Triaryl Diketimines and Diketones
Woo Young Lee*, Youngsoo Kim, Wonbo Sim, Chang Hee Park, Yoon-Mo Ahn, Oee Sook Park
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.
362 - 366
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