Mechanism for oxidation of phenylacetylenes with peroxymonophosphoric acid. Oxirene as an intermediate inconvertible to ketocarbene

Y Ogata, Y Sawaki, T Ohno

Index: Ogata, Yoshiro; Sawaki, Yasuhiko; Ohno, Takashi Journal of the American Chemical Society, 1982 , vol. 104, # 1 p. 216 - 219

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Citation Number: 19

Abstract

Abstract: Peroxymonophosphoric acid (H3P05) is shown to be an effective oxidant for acetylenes. Phenylacetylenes, P h CXR (R= Ph, H, and Me), afford diketones (PhCOCOR), benzoic acid, and rearranged acids (PhRCHC02H). The relative migratory aptitude is in the order of H>> Me> Ph, which is in agreement with the order of H>> Ph-Me for the Wolff rearrangement of a-diazo ketones. However, the oxidation of acetylenes in MeOH-MeCN ...