Synthesis and x-ray analysis of 2,3,5,6,11-pentaoxabicyclo[5.3.1]-undecanes

Masahiro Miura, Akio Ikegami, Masatomo Nojima, Shigekazu Kusabayashi, Kevin J. McCullough, Malcolm D. Walkinshaw

Research output: Contribution to journalArticle

Abstract

The reactions of bicyclic ozonides and aldehyde- or ketone-derived peroxides, preformed or generated in situ, in the presence of chlorosulphonic acid afford the corresponding 2,3,5,6,11 -pentaoxabicyclo-[5.3.1] undecanes. In addition, 1,2,4,5-tetraoxans are often isolated from the product mixture. Mechanisms are proposed to account for the observed peroxidic products. An X-ray analysis of the crystalline product (4b) confirms the general structure and reveals that it is solely the exo-isomer.

Original languageEnglish
Pages (from-to)1657-1664
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1983

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