Thianthrene 5‐oxide (SSO) is established as a useful and convenient chemical probe to assess the electronic character (Xso) of oxygen transfer agents. Thus, H2O2 under basic conditions (HOOH/nBu4NOH) gives an Xso value of 1.00, while H2O2 under acidic conditions (HOOH/HClO4) affords an Xso value near zero. On this Xso scale, dimethyldioxirane (Xso = 0.13 at 0°C) and methyl(trifluoromethyl)dioxirane (Xso = 0.10 at 0°C) are, as expected, definitely strong electrophilic oxidants.
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Adam et al. (1994) studied this question.
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