Electrochemical oxidation and reduction of a substituted alkylidenecyclopropanaphthalene

An electrochemical and spectroelectrochemical study of substituted alkylidenecyclopropabenzenes: 1-(diphenylmethylene)cyclopropabenzene in the first anodic and cathodic voltammetric waves in acetonitrile

“…5). These observations are consistent with a reversible electron transfer followed by kinetic decomposition of the resulting cation radical (5). If the potential is swept immediately to more negative values following the oxidation of I11 to its cation radical, a new peak appears at about -0.7 V (Fig.…”

“…There is no evidence of anion radical decay on the experimental timescale (ca. 1 min); the anion radical is quite stable, as is that of the naphthyl cycloproparene analog (5).…”

From Solvolysis to Self-Assembly

“…However, after Brian’s return to Wellington, the alternative Peterson olefination89 of 39 worked well88; that started a decade-plus long trans-oceanic collaboration90 with Brian, which resulted not only in nearly 20 joint publications, but also a lifelong friendship. In a collaborative fashion we investigated the electrochemical properties,91 photoelectron spectra,92 polarity,93 13 C-NMR94 and ambiphilicity95 of these novel strained hydrocarbons. We explored their reactions with both electrophiles96 and nucleophiles 97.…”

Developments in cycloproparene chemistry

“…148 The diphenylmethylenecycloproparenes 149a/150a each undergo reversible electrochemical reduction and oxidation to give a stable radical anion 163 and a quasi-stable radical cation 164, respectively. 149 The anion 163 RsH or RR = faen20 164 radicals, formed by simple one-electron transfer, are particularly stable but react rapidly with oxygen when it is present. This reaction gives no new organic products but regenerates the alkylidenecycloproparene.…”