1993
DOI: 10.1021/ja00068a082
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Diphenylcarbene cation: electronic and molecular structure

Abstract: Carbene radical ions have been postulated repeatedly as intermediates in the (electro)chemical reduction or oxidation of diazo compounds and other precursors. Bethell and Parker have shown that unimolecular loss ofN2 from ionized diazo compounds does not represent a major reaction pathway in solution except in special cases,2 i.e., the radical cations of diarylcarbenes which are formed upon electrochemical oxidation of the corresponding diazo precursors.3 Such carbene species exhibit both electrophilic and rad… Show more

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Cited by 21 publications
(23 citation statements)
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“…Exhaustive studies have been completed on the rates of reaction of carbenes generated photochemically with organic substrates, but none encompassed the reactivity of such free carbenes towards transition metal complexes to yield carbene complexes. [3][4][5]9,10 Although In both cases, the azine R 2 CN 2 CR 2 (where R = Ph, Tol) was produced in significant quantities and detected by 1 H NMR spectroscopy.…”
Section: Resultsmentioning
confidence: 99%
“…Exhaustive studies have been completed on the rates of reaction of carbenes generated photochemically with organic substrates, but none encompassed the reactivity of such free carbenes towards transition metal complexes to yield carbene complexes. [3][4][5]9,10 Although In both cases, the azine R 2 CN 2 CR 2 (where R = Ph, Tol) was produced in significant quantities and detected by 1 H NMR spectroscopy.…”
Section: Resultsmentioning
confidence: 99%
“…4 Similarly, the diphenylcarbene radical cation has been demonstrated spectroscopically to have the σ ؒ /π ϩ ground state. 5 The spatial separation of spin and charge in these carbene radical cations is expected to result in radical as well as electrophilic reactivity. 2, 5 Indeed, a recent examination of the reactions of the bis(p-methylphenyl)carbene radical cation revealed both types of reactivity, though electrophilic reactivity was more prevalent.…”
Section: Introductionmentioning
confidence: 99%
“…We thus take the DMPO-N• and DMPO-C• signals as an indication of the trapped N-centred diazo radical and C-centred carbene radical adducts. 24,25 The appearance of the three-line DMPOX signal, which was also detected with the reaction system of oxygenation of iridium(II)-ethene (or "iridium(III)-ethyl radical") 26 in the presence of DMPO could support the generation of the open-shell copper complexes with the poly(imidazole-Cu)-EDA system. After reaction, we found the colour of poly(imidazole-Cu) changed from blue to green ( Fig.…”
mentioning
confidence: 90%