On the question of carbonyl oxide intermediates in the oxygen transfer by furan endoperoxides and bicyclic ozonides: intramolecular trapping experiments |
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Authors: | Waldemar Adam Augusto Rodriguez |
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Affiliation: | Departamento de Quimica, Universidad de Puerto Rico, Rio Piedras, Puerto Rico 00931, USA;Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-8700 Würzburg, BRD |
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Abstract: | On heating the furan endoperoxide () rearranges into the enol ester () and the bicyclic ozonide () affords instead the rearranged ozonide (). The process () → () represents an intramolecular Baeyer-Villiger rearrangement presumably via the dioxirane (D-2), while the process () → () represents intramolecular trapping of the carbonyl oxide (C-3). |
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