Compounds with the structure ArNRNCONRNAr (where Ar

Chapter 11, Problem 11.53

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Compounds with the structure ArNRNCONRNAr (where Ar represents an aromatic group) are used in liquid crystal formulations for LCDs (liquid crystal displays) as well as for optical switches and image storage because of their high resolution and sensitivity. However, it has been found recently that, upon irradiation with light at 350 nm, bisphenyl carbodiazone (PhNRNCONRNPh) undergoes homolytic decomposition to give radicals that can be trapped with a tetramethylpiperidinoxyl (TEMPO) radical (Tetrahedron Lett. 2006, 47, 21152118). Propose a mechanism that explains the formation of all three products from this process, shown below. N N N O N O N (TEMPO) Ph N N O O N + + O N Ph N2 h (350 nm

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