N-oxides and related compounds. Part 60. Novel thermal and photochemical rearrangements of N-substituted 2-pyridones
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2743-2754
- https://doi.org/10.1039/p19800002743
Abstract
Examples of four novel rearrangements of derivatives of 1-hydroxy-4,6-diphenyl-2-pyridone are reported: all involve N–O fission and formation of 3-substituted or both 3- and 5-substituted-4,6-diphenyl-2-pyridones. (a) 1-OCH2CH2R (R = vinyl or phenyl) compounds give 3-CH2R (R = vinyl or phenyl) derivatives with elimination of CH2O. (b) The 1-octyloxy-compound gives the 3-octyloxy-derivative by simple transposition. (c) 1-Acyloxy-compounds form the corresponding 3- and 5-acyloxy-2-pyridones. (d) 1-Imidoyloxy-compounds yield the rearranged 3-and 5-amido-2-pyridones. The mechanisms probably all involve homolytic N–O fission.Keywords
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