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Criegee rearrangement of α-alkoxy hydroperoxides a synthesis of esters and lactones that complements the baeyer-villiger oxidation of ketones

✍ Scribed by Stuart L. Schreiber; Wai-Fong Liew

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 212 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)81926-7

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✦ Synopsis

cr-Alkoxy hydroperoxides undergo Criegee rearrangment upon treatment with (CH,CO),O to provide esters or lactones. The acylation of hydroperoxides results in the formation of peroxyesters which can undergo the Criegee rearrangement to afford ketones or ketals.' We have studied the acylation of an a-alkoxyhydroperoxide to furnish a peroxyester that is related to the intermediate produced in the Baeyer-Villiger reaction.3 The peroxyester undergoes the Criegee rearrangement to a dioxenium ion that suffers dealkylation or hydrolysis to provide an ester or a lactone.

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