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On the question of carbonyl oxide intermediates in the oxygen transfer by furan endoperoxides and bicyclic ozonides: intramolecular trapping experiments
Authors:Waldemar Adam  Augusto Rodriguez
Institution: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
Abstract:On heating the furan endoperoxide (2) rearranges into the enol ester (4) and the bicyclic ozonide (3) affords instead the rearranged ozonide (7). The process (2) → (4) represents an intramolecular Baeyer-Villiger rearrangement presumably via the dioxirane (D-2), while the process (3) → (7) represents intramolecular trapping of the carbonyl oxide (C-3).
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