Studies on the mechanism of decomposition of 1-methyl-1-(1-naphthyl)ethyl hydroperoxides to 2-(1-naphthyloxy)propenes |
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| Authors: | Beata Orlińska Jan Zawadiak Roman Mazurkiewicz Zbigniew Stec and Henryk Koroniak |
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| Institution: | (1) Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Gliwice, Poland;(2) Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Gliwice, Poland;(3) Faculty of Chemistry, Adam Mickiewicz University, Poznan, Poland |
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| Abstract: | Abstract Thermal decomposition of 1-methyl-1-(4-methyl-1-naphthyl)ethyl hydroperoxide under gas chromatography-mass spectroscopy (GC–MS)
conditions gives 2-((4-methyl-1-naphthyl)oxy)propene as the main product (50.5%), without any detectable traces of the isomeric
2-((5-methyl-1-naphthyl)oxy)propene. This finding excludes the rearrangement pathway of 1-methyl-1-(1-naphthyl)ethyl hydroperoxides
to the corresponding 2-(1-naphthyloxy)propenes, which involves formation of a naphthofuran derivative as an intermediate and
transfer of the isopropenyloxy group to the 8 position. This result, as well as our previous density functional theory (DFT)
calculations, points to the rearrangement pathway involving an oxirane-type intermediate as the most plausible pathway to
2-(1-naphthyloxy)propenes. This rearrangement is responsible for the unusual inhibition effects of 1-methyl-1-(1-naphthyl)ethyl
hydroperoxide on the liquid-phase oxidation of isopropylarenes with oxygen. |
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