The Photochemistry of 3- and 4-Nitro Phenyl Azides
Liang, Tsuei-Yun
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https://hdl.handle.net/2142/70372
Description
Title
The Photochemistry of 3- and 4-Nitro Phenyl Azides
Author(s)
Liang, Tsuei-Yun
Issue Date
1987
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
The photochemistry of 4-nitro and 3-nitrophenyl azides in inert and reactive solvents was examined. Photolysis of nitrophenyl azides in solution at room temperature or in a frozen glass at 77 K gives triplet nitrenes. The products of the reaction of triplet nitrenes depend on the power of the light source. Triplet 4-nitrophenyl nitrene dimerizes to form azobenzene at a diffusion controlled rate and reacts with the tertiary amine by single-electron transfer. The rate constant of the reaction of triplet nitrenes with O$\sb2$ is ca. 10,000 fold slower than the dimerization. The precursors of the triplet nitrenes can be trapped by secondary amines. The mechanisms of these reactions are discussed.
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