Quinone Methides, and Benzoxetenes
| dc.contributor.author | Adam, W. | en |
| dc.contributor.author | Hadjiarapoglou, L. | en |
| dc.contributor.author | Peters, K. | en |
| dc.contributor.author | Sauter, M. | en |
| dc.date.accessioned | 2015-11-24T16:56:19Z | |
| dc.date.available | 2015-11-24T16:56:19Z | |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/10416 | |
| dc.rights | Default Licence | - |
| dc.title | Quinone Methides, and Benzoxetenes | en |
| heal.abstract | Low-temperature oxidation of the four possible regioisomeric methoxy-substituted benzofurans 1 by dimethyldioxirane afforded the rather labile epoxides 2, which are in equilibrium with their equally labile quinone methides 3 through reversible valence isomerization. Photochemical cyclization of the latter afforded the hitherto unknown benzoxetenes 4, which are sufficiently persistent at subambient temperatures to permit spectral characterization. The labile oxetenes 4 slowly revert to the same equilibrium mixtures of the epoxides 2 and quinone methides 3 as are obtained in the dioxirane epoxidation of the benzofurans 1. The mutual transformations of the benzofuran epoxides 2, quinone methides 3, and benzoxetenes 4 include thermal isomerization to the allylic alcohols S and their ring-opened tautomers S"™, nucleophilic trapping in the form of the methanol adducts 6 and their ring-opened tautomers 6"™, inverse Diels-Alder reaction to the [4 + 21 cycloadducts 7, and the 1,3-dipolar cycloaddition products 8 with tetracyanoethylene (TCNE). | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | 10.1021/ja00072a012 | - |
| heal.identifier.secondary | http://pubs.acs.org/doi/abs/10.1021/ja00072a012 | - |
| heal.journalName | J. Am. Chem. Soc. | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 1993 | - |
| heal.publisher | American Chemical Society | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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