Abstract
Thermochemical cycles show that deprotonation of alkane radical cations is an exothermic process, and indeed photoinduced SET between several alkanes and 1,2,4,5-tetracyanobenzene (TCB) is followed by efficient deprotonation of the radical cation with tertiary > secondary > primary selectivity; the alkyl radical is trapped by TCB˙– or, when present, by oxygen; when tetrachloro-p-benzoquinone is used in the place of TCB, the radical is further oxidized to the cation.
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