precipitation may have prevented further oxidation table 1 lists the variety of conditions that were attempted to effect photooxygenation of hpiw to polyformylhexaazaisowurtzitane derivatives the products of some photooxygenation reactions were subjected to nitrolysis after isolation from reaction suspensions by removal of all volatiles solvent and acetaldehyde by product an initial run utilizing a mixture of about 98 nitric acid and acetonitrile d 3 produced a minor amount of cl 20 lt 10 u2014 confirmed by hplc analysis as well as 1 h and 13 c nmr spectrometry u2014 in a complex mixture after 6 days of reaction at ambient temperature such pro longed reaction conditions significantly hydrolyzed acetonitrile ultimately to acetic acid in another run the very viscous oily residue from a photooxygenation reaction was subjected to nitrolysis conditions using about 98 nitric acid in the presence of nafion nr50 beads as a strong br u00f8nsted acid catalyst equation 3 nafion u00ae resins are perfluorinated ion exchange materials composed of carbon fluorine backbone chains and perfluoro side chains containing sulfonic acid groups nafion nr50 is a polymer of the general structure the application of nafion u00ae resins as versatile heterogeneous catalysts in organic transformations has been well established aldrich technical bulletin al 163 and references therein other known strong br u00f8nsted acid catalysts may be screened for efficiency in promoting this conversion and those being efficacious will be suitable replacements for nafion nr50 reflux of the reaction solution for a.