1998
DOI: 10.1002/chin.199824079
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ChemInform Abstract: Multistep Reversible Redox Systems. Part 63. 2,5‐Disubstituted N,N′‐Dicyanoquinone Diimines (DCNQIs) — Syntheses and Redox Properties.

Abstract: 1998 quinone derivatives quinone derivatives Q 0410 24 -079 Multistep Reversible Redox Systems. Part 63. 2,5-Disubstituted N,N'-Dicyanoquinone Diimines (DCNQIs) -Syntheses and Redox Properties. -Quinones such as (I) and dicyanoquinone diimines such as (II) are synthesized in order to study substituent effects. Both (I) and (II) undergo reversible electron transfer in 2 steps including thermodynamically very stable radical cations. The crystal structures of some quinones are presented. -(HUENIG, S.; BAU, R.; KE… Show more

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“…The bromide 13 was accessible from 1,4-dimethoxy-2-methylnaphthalene 10 through bromination at the aromatic ring with Br 2 in CH 2 Cl 2 at 0 °C to the bromide 11 (86%) and then replacement of the bromine by the CF 3 group using (trifluoromethyl)copper . This reagent can be produced from CF 3 CO 2 Na and CuI by decarboxylation in toluene/DMA at high temperatures . After 8 h at 150−170 °C the 1,4-dimethoxy-2-methyl-3-trifluoromethylnaphthalene 12 was isolated in 46% yield next to 33% of the unreacted bromide 11 .…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The bromide 13 was accessible from 1,4-dimethoxy-2-methylnaphthalene 10 through bromination at the aromatic ring with Br 2 in CH 2 Cl 2 at 0 °C to the bromide 11 (86%) and then replacement of the bromine by the CF 3 group using (trifluoromethyl)copper . This reagent can be produced from CF 3 CO 2 Na and CuI by decarboxylation in toluene/DMA at high temperatures . After 8 h at 150−170 °C the 1,4-dimethoxy-2-methyl-3-trifluoromethylnaphthalene 12 was isolated in 46% yield next to 33% of the unreacted bromide 11 .…”
Section: Resultsmentioning
confidence: 99%
“…In all cases we recovered the unreacted starting material, which was then recycled. Finally, the bromination of the methyl group in 12 with N- bromosuccinimide in CCl 4 and benzoyl peroxide as initiator , gave 55% of the desired 2-bromomethyl-1,4-dimethoxy-3-trifluoromethylnaphthalene 13 . For the synthesis of the dual drugs 14 and 15 (Scheme ), amodiaquine and paracetamol were respectively deprotonated with cesium hydroxide in DMF together with molecular sieves and then coupled with the bromide 13 .…”
Section: Resultsmentioning
confidence: 99%