ORGN 536

        The direct incorporation of a silver development inhibitor into Ektachrome films may require the reagent’s deactivation to mitigate disadvantageous interactions.  During film development, this masked reagent must be released to afford its desired effects.  Inhibitor releasing quinones (IRQ’s) were designed for this purpose.  These benzoquinone derivatives serve to mask the inhibitor’s thiol group prior to film development, then via cross-redox reaction, provide active inhibitor during film processing.  The synthesis of such a new compound, IRQ-1, has now been thoroughly evaluated for potential multi-kilogram synthesis.  Several new reaction protocols were developed; a detailed summary of its synthesis is presented.  Of particular interest are (1) the decarboxylative alkylation of 1,4-nathoquinone with 1,12-dodecanedicarboxylic acid; (2) the back-ring hydrogenation of this naphthoquinone; and (3) the formation and oxidative cleave of a benzoxazine to provide an aminoquinone.  Aspects of its photographic chemistry will also be discussed.