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EPR study of radical intermediates from the oxidation of 6-ethoxy-2,2,4-trimethyl- and 6-ethoxy-2,2,4,8-tetramethyl-1,2-dihydroquinoline

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Author(s)

Frank D. Gunstone, Raphael C. Mordi, Snorri Thorisson, John C. Walton, Richard A. Jackson

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Abstract

The EPR spectra of 1,2-dihydro-6-ethoxy-2,2,4-trimethyl- and 1,2-dihydro-6-ethoxy-2,2,4,8-tetramethyl-quinolin-1-yl radicals were observed in heptane solution. The hyperfine splittings showed that this class of radical is extensively delocalised with significant spin density at C(8). Both radicals decayed by second-order processes, the rate constants being 5 × 106 and 4 × 102 dm3 mol-1 s-1, respectively at 273 K. The latter reaction is much slower because the 8-methyl substituent blocks the formation of the 1,8′-dimer. Both radicals reacted with oxygen to give the corresponding nitroxides, although reaction was very slow for the 8-methyl derivative. A mechanism is proposed to rationalise product formation from 1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline when used as an antioxidant.

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Details

Original languageEnglish
Pages (from-to)1955-1958
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number12
Publication statusPublished - 1 Dec 1991

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