Chapter 4 Test Form 2C Answer Key UPD
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Thermolysis of the triazide 2 was studied previously by us and it was found that under conditions which are slightly different from those used in this paper, thermolysis occurs in two steps. First, decomposition of the azido group leads to elimination of H2O to give the corresponding azide, N3. Then, the azide ring with N3 breaks and the azido group is reduced to the azaarene, which in the same study underwent a second decomposition step to give CO2 and N2. This decomposition of the azaarene, with elimination of N2 and one CO2 molecule, was the proposed mechanism for the thermolysis of compound 2 in two steps. We now show that this thermal transformation is more complex. The thermolysis of compound 2 in air under continuous stirring at 100 °C proceeds in a single step via elimination of N2 to give a compound 22. The latter decomposes further to a compound 23 which is produced in small amounts (1–5%) due to breakdown of 22. The main product of thermolysis, which is the major compound detected in the gas phase, is compound 24. In all three compounds, the azido group is not protected by the triazide bridge and is therefore reductively cleaved to form the corresponding azaarene ring. However, in these three compounds, the mechanism of the thermolysis of the azaarene ring is dramatically different. In compound 24, azaarene ring opening occurs to form an azaarene arene, which then undergoes decarboxylation to the carboxylic acid, which then converts into a nitrile. In compounds 22 and 23, the opening of the azaarene ring gives rise to an initial azaarene species, which reacts to form iminium ion 25, which then decomposes via rearrangement to the azide, which subsequently eliminates N2 to form compound 24.
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