Condensation of 4-substituted phthalonitriles with lithium 2-N,N-dimethylaminoethoxide in 2-N,N-dimethylamino-ethanol gives a non-statistical mixture of tetrasubstituted phthalocyanines at room temperature or lower while 3-substituted phthalonitriles similarly condense with lithium octan-1-olate in octan-1-ol giving 1,8,15,22-tetra-substituted phthalocyanines as pure isomers.
C. C. Leznoff, M. Hu and K. J. M. Nolan, Chem. Commun., 1996, 1245 DOI: 10.1039/CC9960001245
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