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Issue 2, 1999
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Formation of secondary ozonides in the gas phase low-temperature ozonation of primary and secondary alkenes

Abstract

The gas-phase ozonation of a series of alkenes RCH[double bond, length half m-dash]CH2 (R = Et, Hex), trans-RHC[double bond, length half m-dash]CHR (R = Me, Et, Pri) and Me2C[double bond, length half m-dash]CMe2 at –40 to 20 °C, and that of ethene H2C[double bond, length half m-dash]CH2 at –120 to 0 °C at 10–4 v/v concentrations in N2 at atmospheric pressure have been studied. Using complementary product analysis by means of GC–FTIR and GC–MS techniques, we present conclusive evidence for the formation of secondary alkene ozonides as high-yield products in all instances except Me2C[double bond, length half m-dash]CMe2. It is shown that the stereoselectivity for the conversion of trans-RHC[double bond, length half m-dash]CHR (R = Me, Et, Pri) to trans-secondary ozonides in the gas phase is similar to that observed earlier in solution, and that the yields of secondary ozonides from RHC[double bond, length half m-dash]CH2, but not those from RHC[double bond, length half m-dash]CHR, significantly decrease with increasing temperature.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1999, 239-248
Article type
Paper

Formation of secondary ozonides in the gas phase low-temperature ozonation of primary and secondary alkenes

R. Fajgar, J. Vítek, Y. Haas and J. Pola, J. Chem. Soc., Perkin Trans. 2, 1999, 239
DOI: 10.1039/A807208F

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