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Reactivity and Product Analysis of a Pair of Cumyloxyl and tert-Butoxyl Radicals Generated in Photolysis of tert-Butyl Cumyl Peroxide.

Alkoxyl radicals play important roles in various fields of chemistry. Understanding their reactivity is essential to applying their chemistry for industrial and biological purposes. Hydrogen atom transfer and C-C β-scission reactions have been reported from alkoxyl radicals. The ratios of these two processes were investigated using the cumyloxyl (CumO•) and tert-butoxyl radicals (t-BuO•), respectively. However, the products generated from the pair of radicals have not been investigated in detail. In this study, CumO• and t-BuO• were simultaneously generated from the photolysis of tert-butyl cumyl peroxide to understand the chemical behavior of the pair of radicals by analyzing the products and their distribution. Electron paramagnetic resonance and/or transient absorption spectroscopy analyses of radicals, including CumO• and t-BuO•, provide more information about the radicals generated during the photolysis of tert-butyl cumyl peroxide. Furthermore, the photoproducts of (3-(tert-butylperoxy)pentane-3-yl)benzene were investigated to understand the reaction mechanism of product formation for in-cage versus out-of-cage products. The triplet-sensitized reaction induced by acetophenone, which is produced from CumO•, was also examined to understand the spin-state effect on product distribution.