Thermally Induced And Base Catalyzed Reactions Of Naphthoquinone Diazides

Abstract

Thermally induced and base catalyzed reactions of a phenol ester of 1,2-naphthoquinone-diazide-5-sulfonic acid (DAM) with p-cresol were investigated. In total seven reaction products were obtained for the thermally induced reaction. The three major products, TR--F4, TR-F6 and TR-F7, were isolated and their structures were determined by means of several advanced spectroscopic techniques like Fourier transform nuclear magnetic resonance (FTNMR) and field desorption mass spectroscopy (FD-MS). Besides a cresol ester of indenecarboxylic acid (TR-F6) and an azo compound which contains two DAM originated moieties and cresol (TR-F7), the formation of a novel compound was found; a phenol ester of 2-cresyl-l-naphthol-5-sulfonic acid. On the other hand, four reaction products were found in the base (a 2.38wt% tetramethylammonium hydroxide aq. solution) catalyzed reaction products of DAM with p-cresol, and two major products, BC-Fl and BC-F3, which appeared at the initial stage of the reaction were isolated. The structure determination of the two major products was carried out in the same manner as described above. It was discovered that BC-Fl was a cresol ester of 1-naphthol while BC-F3 was an azoxy compound. Brief discussions will be made on those reactions of naphthoquinone diazides with a matrix novolak resin with reference to the results obtained by the present study.