Cycloadditions between carbonyl oxides and dicarbonyl compounds: Isolation and characterisation of novel polycyclic 1,2,4,6-tetroxepane derivatives

Kevin J. McCullough, Toshiya Sugimoto, Shogo Tanaka, Shigekazu Kusabayashi, Masatomo Nojima

Research output: Contribution to journalArticle

Abstract

Formaldehyde O-oxide reacts with dicarbonyl compounds to produce mono-ozonides formed by conventional [3 + 2] cycloadditions to an aldehydic carbonyl group of the substrate, and/or polycyclic 1,2,4,6-tetroxepane derivatives arising from formal [3 + 2 + 2] cycloadditions involving both carbonyl groups. Similar reactions between the more highly substituted carbonyl oxides, benzaldehyde and octanal O-oxides, and dicarbonyl compounds yielded the corresponding mono-ozonides as the sole isolable cycloaddition products. In certain favourable cases, mono-ozonides could undergo acid-catalysed intramolecular rearrangement to the corresponding 1,2,4,6-tetroxepanes. X- Ray crystallographic analyses of two 1,2,4,6-tetroxepanes. 6a and 13b, are recorded.

Original languageEnglish
Pages (from-to)643-651
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number6
Publication statusPublished - 1994

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