Aromatic stabilization in the transition state is used to develop a new approach to the study of one- and two-electron oxidations involving hydrogen transfer. 2,3-Dichloro-5,6-dicyanobenzoquinone is shown to react with tropilidene and 1,2,3-triphenylcyclopropene 10⁴ to 10⁵ times faster than with simple model compound. This high reactivity is interpreted by aromatic stabilization in the transition state of the rate-limiting step and considered as additional evidence for hydride ion transfer. The high reactivity of 1,4-dihydrobenzene is discussed and interpreted as suggesting the simultaneous removal of two hydrogen atoms.