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Benzocyclobutene— o -xylylene valence tautomerization: Oxygen and sulfur analogs
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| Zeitschriftentitel: | Proceedings of the National Academy of Sciences |
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| Personen und Körperschaften: | , |
| In: | Proceedings of the National Academy of Sciences, 77, 1980, 4, S. 1732-1735 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Proceedings of the National Academy of Sciences
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| Schlagwörter: |
| Zusammenfassung: | <jats:p> Gas phase pyrolysis of <jats:italic>o</jats:italic> -hydroxybenzyl alcohol at 750°C gave <jats:italic>o</jats:italic> -quinonemethide, which, on isolation, formed a mixture of the corresponding dimer and trimer. However, pyrolysis of <jats:italic>o</jats:italic> -hydroxy-[1-(4-pentenyl)]benzyl alcohol permitted intramolecular trapping of the intermediate <jats:italic>o</jats:italic> -quinonemethide, giving 3,4-trimethylene-3,4-dihydrobenzochroman. In contrast, gas phase pyrolysis of <jats:italic>o</jats:italic> -mercaptobenzyl alcohol readily gave benzo[ <jats:italic>b</jats:italic> ]thiete in good yield. The pyrolysis makes this interesting highly strained molecule readily available for study and synthetic application. Preliminary results showed that benzo[ <jats:italic>b</jats:italic> ]thiete readily undergoes thermal dimerization, ring-opening reactions with nucleophiles, and a variety of Diels-Alder reactions. </jats:p> |
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| Umfang: | 1732-1735 |
| ISSN: |
0027-8424
1091-6490 |
| DOI: | 10.1073/pnas.77.4.1732 |