1027986-13-5Relevant academic research and scientific papers
Sterically hindered carbonyl O-oxides and dioxiranes - (6-tert-butyl-2,3,4- trimethylphenyl)phenylcarbonyl O-oxide and (6-terf-butyl-2,3,4-trimethylphenyl) phenyldioxirane
Scliroeder, Kerstin,Sander
, p. 496 - 504 (2007/10/03)
(6-terf-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.
