Abstract
Abstract(6‐tert‐Butyl‐2,3,4‐trimethylphenyl)phenylcarbonyl O‐oxide (1b) was generated by photooxidation of diazo compound 6b in an organic glass and in solution and characterized by UV/Vis spectroscopy and by its photo‐ and thermochemistry. With 4.5 min at 230 K the half‐life of 1b is considerably smaller than that of dimesityl ketone O‐oxide (1a). The only clearly detected thermal product of 1b is the corresponding ketone 3b. The isomeric (6‐tert‐butyl‐2,3,4‐trimethylphenyl)phenyldioxirane (2b) could also be synthesized and characterized by NMR spectroscopy. With a half‐life time of 20 min at 20 °C this dioxirane rearranges to the isochroman derivative 11 as the only product. Plausible mechanisms for this rearrangement, which involves the hydroxylation of a non‐activated C−H bond, are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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