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THE PHOTOCHEMICAL SYNTHESIS OF POLYAZACYCLOBUTANE SYSTEMS.
Final rept., 15 Nov 63-31 Aug 65,
OHIO STATE UNIV RESEARCH FOUNDATION COLUMBUS
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Nineteen Schiff bases, both acyclic and cyclic, were prepared in order to study their behavior on ultraviolet irradiation a in the solid state and b in solution, c both in the presence and absence of oxygen and d with and without a Pyrex filter. Most of the Schiff bases were found to be remarkably stable to ultraviolet light and only the starting materials could be isolated. On prolonged irradiation, dark brown tarry products were also formed. In contrast, irradiation of the Schiff base formed from 1-naphthaldehyde and 1-naphthyl amine gave dibenzo c,k phenanthridine similarly, the Schiff base from 1-naphthaldehyde and toluidine gave the analogous phenanthridine. 1,2,5Naphtho b thiadiazole was synthesized and photolyzed in the hope that 1,2-diazanaphtho b cyclobutadiene might be produced, but photodimerization of the thiadiazole was the only reaction observed. Finally, a new photolytic decomposition of benzylic sulfones was discovered and investigated in detail. Author
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