Evidence for the HOOO- anion in the ozonation of 1,3-dioxolanes: hemiortho esters as the primary products

Božo Plesničar, Janez Cerkovnik, Tell Tuttle, Elfi Kraka, Dieter Cremer

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Low-temperature ozonation (-78 °C) of 2-methyl-1,3-dioxolane (1a) in acetone-d6, methyl acetate, and tert-butyl methyl ether produced both the corresponding acetal hydrotrioxide (3a, ROOOH) and the hemiortho ester (2a, ROH) in molar ratio 1:5. Both intermediates were fully characterized by 1H, 13C, and 17O NMR spectroscopy, and they both decomposed to the corresponding hydroxy ester at higher temperatures. The mechanism involving the HOOO- anion formed by the abstraction of the hydride ion by ozone to form an ion pair, R+ -OOOH, with its subsequent collapse to either the corresponding hemiortho ester (ROH) or the acetal hydrotrioxide (ROOOH) was proposed. This mechanism is supported by the PISA/B3LYP/6-311++G(3df,3pd) calculations.

Original languageEnglish
Pages (from-to)11260-11261
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number38
Early online date28 Aug 2002
DOIs
Publication statusPublished - 25 Sep 2002

Keywords

  • low-temperature ozonation
  • decomposition
  • organic materials

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