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03 de decembro de 2012 Mecanismos das Reacciéns Orgénicas: Proba Reacciéns Periciclicas NOME Mote Cohucoc. Qc 1, Pyrolisis of compound 1 at 460 °C gave a diene whose \ (p.m) 6.06 (1H, dd, J = 10.3 and 12.1 Hz), 6.23 (1H, dd, |= 103 ana t+ 1= 14.7 Hz) and 7.32 (1H, d,J = 12.1 Hz). Does this agree with the this diene formed and why does it have that stereochemistry? R spectrum included 6(H) 631 (1H, d, re given, How is DL 460°C, h ee co ON SPI AcO SPh 2. Thioketones, with a C=S bond, are not usually stable. However, this thioketone is quite stable and undergoes reaction with maleic anhydride to give the product shown. Comment the mechanism of the reaction and the stereochemistry ofthe product. 9° Crs “Op ° 3. This unsaturated alcohol (pent-1,7,9-trien-3-ol) is perfectly stable until it is oxidized with Cr(VI}: it then immediately cyclizes to a single product. Suggest a structure for the OH ae oe om FFTs OoE 4. Bromocyclooctatetraene rearranges to trans-B-bromostyrene. The rate of the in gyargement is solvent dependent, the first order rate constant increasing from 107.04 in cyclohexane to 103 5 in acetonitrile at 80 °C. In the Presence of lithium iodide, the Product is trans-B-iodostyrene, although trans-f-bromo styrene is unaffected by lithium ‘odide under the conditions of the reaction. Suggest a mechanism for this rearrangement,