1989
DOI: 10.1002/macp.1989.021900111
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Electron transfer from carbanionic salts to linear sequences of conjugated double bonds, 2. Reaction with trans‐β‐carotene

Abstract: The reactions of a set of organoalkaline compounds with trans-p-carotene (Car) were studied in solution (using UV/Vis, ESR, and mass spectroscopy) and compared with the reactions of the same set with insoluble polyacetylene. It was shown that the naphthalene radical ion and the dicarbanionic dimer of 1, I-diphenylethylene, 1,1,4,4-tetraphenyl-l,4-butanediide, react with Car by a simple electron transfer leading to Car radical ion and dianion. This dianion is protonated by methanol mainly at carbon 7 or 7'. On … Show more

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Cited by 8 publications
(7 citation statements)
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“…[18] Therefore, the prompt appearance of Car 2-3 suggests either a direct two electron uptake, a rapid, successive one-electron attachment or a single electron uptake followed by an immediate disproportionation reaction 2 Car ·-Ǟ Car 2-+ Car. [14] A probable dimerisation 2 Car ·-Ǟ Car-Car 2-has been excluded. [33] Despite exhaustive investigations the mechanistic evidence for electron transfer reactions in alkaline DMSO remains uncertain: a cryptically formulated multistep addition reaction of DMSO -with dicarbonyl compounds was explicitly presented as "belief ".…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…[18] Therefore, the prompt appearance of Car 2-3 suggests either a direct two electron uptake, a rapid, successive one-electron attachment or a single electron uptake followed by an immediate disproportionation reaction 2 Car ·-Ǟ Car 2-+ Car. [14] A probable dimerisation 2 Car ·-Ǟ Car-Car 2-has been excluded. [33] Despite exhaustive investigations the mechanistic evidence for electron transfer reactions in alkaline DMSO remains uncertain: a cryptically formulated multistep addition reaction of DMSO -with dicarbonyl compounds was explicitly presented as "belief ".…”
Section: Resultsmentioning
confidence: 99%
“…[9] So far, electron uptake by Car has been investigated by quite elaborated methods: chemical reactions with metals (Al-Hg, Na, K, Cs), [10][11][12][13] and metal organic compounds (e.g. sBuLi), [14] electrochemical methods, [15] ionizing rays (pulse radiolysis) [2,16,17] and flash photolysis. [18] Notwithstanding, electron transfer to Car should be possible without relying on particular scrupulous procedures.…”
Section: ·-mentioning
confidence: 99%
“…The commercial /3-carotene was purified and carefully handled as previously described with necessary precautions to avoid any trace of proton donors. 10 The /3-carotene dianion was synthesized in a glass apparatus provided with a glass filter and optical cell, which was flamed and sealed under vacuum, by reacting a THF solution of /3-carotene over a sodium mirror. The resulting solution was filtered through a coarse frit into the quartz cell.…”
Section: Methodsmentioning
confidence: 99%
“…Figure10. Optical spectral changes observed during the transformation of /3-carotene radical anion Bu4N+ (Amax = 815) to /3-carotene (A",x = 458) and /3-carotene monoanion Bu4N+ (Amax = 760): (a) /3-carotene, (1) t = 0, (2) t = 20 h, (3) t = 50 h, (4) t = 10 days.…”
mentioning
confidence: 99%
“…Such compounds ought to be included in a forthcoming extended register. Enlarging the selection criteria to <C20 chains, to xenobiotic C,H,O carotenoids, considering heteroatoms outside the carotenoid carbon skeleton sphere and taking into account ionic bounded heteroatoms is desirable for future compilation [36,37]. It would furthermore be valuable to have at hand a complete directory of isotope-substituted carotenoids (D, T, 13 C, 14 C) [38,39,40].…”
Section: Selection Criteriamentioning
confidence: 99%