Reactions of phthalonitriles with carbohydrates and alkali: phthalocyanineand oligomer formation

Reducing sugars and sodium hydroxide react with phthalonitrile and 4-methox yphthalonitrile to form mixtures of the phthalocyanine and oligomers. The o ligomers, obtained in yields up to 54%, were deduced to have a structure th at is predominantly polyazine with the o-cyanophenyl group as a substituent from elemental analysis and spectral data. Since carbohydrate related comp ounds lacking the reducing linkage gave no products, it is suggested that t he observed reactions require the alpha -hydroxycarbonyl grouping. Copyrigh t (C) 2001 John Wiley & Sons, Ltd.