In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene, metal-free phthalocyanine was obtained by heating phthalonitrile in alcohols. Addition of a copper(II) salt in the reaction gave copper phthalocyanine in a good yield.
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Tomoda et al. (1980) studied this question.
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