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17.9.2.5 Method 5: From 2-Cyanobenzamide

DOI: 10.1055/sos-SD-017-01835

McKeown, N. B.Science of Synthesis, (2004171255.

A study of the properties of 2-cyanobenzamide in 1907 produced an insoluble blue material that with hindsight can be attributed to the formation of phthalocyanine.[‌31‌] Linstead found that the cyclotetramerization of 2-cyanobenzamide in the presence of a metal or metal salt in a bulk reaction or in solution is useful for the preparation of unsubstituted metal phthalocyanines 1 (Scheme 14).[‌36‌,‌67‌] Phthalocyanines that are produced readily from 2-cyanobenzamide include PcMg,[‌36‌] PcSiCl2,[‌210‌] PcMn,[‌67‌] PcFe,[‌36‌,‌67‌] PcCo,[‌36‌] PcNi,[‌36‌,‌67‌] PcGeCl2,[‌213‌,‌214‌] PcRuCl,[‌196‌,‌198‌,‌215‌,‌216‌] PcRhCl,[‌217‌,‌218‌] PcOs,[‌219‌,‌220‌] and PcIrCl.[‌220‌]

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