Thianthrene 5‐Oxide (SSO) as a Mechanistic Probe of the Electrophilic Character in the Oxygen Transfer by Dioxiranes
- 1 June 1994
- journal article
- research article
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 127 (6) , 1111-1113
- https://doi.org/10.1002/cber.19941270621
Abstract
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.Keywords
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