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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The thermal decompositions of 2-methyl-2-phenoxypropane

NJ Daly, SA Robertson and LP Steele

Australian Journal of Chemistry 34(2) 343 - 348
Published: 1981

Abstract

The thermal reactions of 2-methyl-2-phenoxypropane have been studied in gas phase over the range 600-670 K by quadrupole mass spectrometry and pressure studies. The reaction is shown to be a homogeneous first-order elimination of phenol and 2-methylpropene which is described by the Arrhenius equation

k = 1014.10±0.12exp[(-210.46±1.36)/RT] s-1

Possible reaction mechanisms are considered and the reaction is found to be a unimolecular elimination rather than a radical chain process initiated by homolysis to phenoxy and 1,1-dimethylethyl radicals. Evidence for the rearrangement to 4-t-butylphenol previously proposed has been carefully sought and it is concluded that the process does not occur in the gas phase. The A-factor observed for the reaction is in good agreement with that calculated for the four-centred transition state proposed for elimination of 2-methylpropene from alkoxypropanes.

https://doi.org/10.1071/CH9810343

© CSIRO 1981

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