Halonium ion-mediated reaction of unsaturated hydroperoxy acetals. Competition between the formation of cyclic peroxides and the migration of the methoxy (or hydroxy) group

Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough

Research output: Contribution to journalArticle

Abstract

Monoozonolyses of dienes 2 in methanol gave in each case the corresponding unsaturated a-methoxy hydroperoxides 3. Capture of 2-alkyl- substituted cyclohexanone oxides by methanol was highly diastereoselective, thereby providing exclusively the hydroperoxides derived from attack by methanol from the less hindered face of the carbonyl oxide intermediates. Halonium ion-mediated reactions of the hydroperoxides 3 gave the novel methoxy- or hydroxy-migrated products, together with the expected halogen- substituted 1,2-dioxanes and/or 1,2-dioxepanes, the composition of the product mixture being a function of the halogenating agent utilized and the structure of 3.

Original languageEnglish
Pages (from-to)1069-1075
Number of pages7
JournalJournal of Organic Chemistry
Volume65
Issue number4
DOIs
Publication statusPublished - 25 Feb 2000

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