| Popis: |
Gas phase pyrolysis of o -hydroxybenzyl alcohol at 750°C gave o -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of o -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate o -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of o -mercaptobenzyl alcohol readily gave benzo[ b ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ b ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. |
