Reducing versus basic properties of 1,2-diaryl-1,2-disodioethanes

Azzena, Ugo; Dettori, Giovanna; Pisano, Luisa; Pittalis, Mario

doi:10.1016/j.tet.2011.03.037

Cited by 8 publications

(17 citation statements)

References 37 publications

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“…The reactivity of 1a, taken as a model compound, was investigated in some detail. In agreement with previous results obtained with halogenated aromatic carboxylic acids [25][26][27], reaction of 1a with either Li or Na metal did not result in any cleavage reaction (Table 1, entries 1 and 2). In contrast, reaction of 1a with an excess of homogeneous reducing agents, like LiN (2a) or NaN (2b), resulted in the quantitative cleavage of the aromatic carbon-chlorine bond ( Table 1, entries 3 and 4).…”

Section: Resultssupporting

confidence: 92%

“…From this point of view, the employment of alkali metals as effective single electron transfer (SET) reducing agents is developing as an interesting alternative in the chemical transformation of hazardous organic halogen atoms into non-toxic halide ions [24][25][26][27]. However, despite their ready availability and high reducing power [28], only two reports concern the reductive dehalogenation of chlorophenols with Na metal in liquid ammonia [29,30].…”

Section: Introductionmentioning

confidence: 99%

“…Following our interest in the field [25][26][27], we now wish to report on the effectiveness of active soluble forms of alkali metals in promoting the reductive degradation of chlorinated phenols under electron transfer reaction conditions in an ethereal solvent, either under stoichiometric or catalytic reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

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Active-alkali metal-promoted reductive cleavage of chlorinated phenols

et al. 2012

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We investigated the degradation of chlorinated phenols under reductive electron transfer reaction conditions. Although Li and Na metal proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Additionally, efficient dehalogenation of the sodium salts of several mono-, di-, and tri-chlorophenols was obtained by their reduction with an excess of Na metal and a catalytic amount of naphthalene.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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Active-alkali metal-promoted reductive cleavage of chlorinated phenols

et al. 2012

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“…We have already reported that reaction of THF solutions of vic ‐dianions 2a , 2b , 2c with halogenated arylacetic acids led to a competition between reductive dehalogenation and α‐metalation, thus disclosing the employment of these diorganometals as bases in the generation of the enediolates of carboxylic acids (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

“…Quenching with D 2 O was realized by adding 0.75 ml of the electrophile to the reaction mixture, followed by aqueous work‐up as described above. Reaction products were analyzed and characterized ( 1 H NMR and IR) by comparison with literature data …”

Section: Methodsmentioning

confidence: 99%

A green solvent approach to the chemistry of 1,2‐diaryl‐1,2‐disodioethanes

Azzena

Kondrot

Pisano

et al. 2012

Applied Organom Chemis

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We investigated the generation and the reactivity of selected 1,2‐diaryl‐1,2‐disodioethanes employing cyclopentyl methyl ether and 2‐methyltetrahydrofuran as green solvent alternatives to tetrahydrofuran. Both solvents proved suitable for the generation of these vic‐diorganometals, as well as for their employment as single‐electron transfer reagents. On the other hand, 2‐methyltetrahydrofuran appears as the solvent of choice in reactions involving the employment of these diorganometals as nucleophiles or bases. Accordingly, our results disclose an environmentally more sustainable approach to the chemistry of these diorganometals and, in a wider sense, to reductive metalation reactions. Copyright © 2012 John Wiley & Sons, Ltd.

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ChemInform Abstract: Reducing versus Basic Properties of 1,2‐Diaryl‐1,2‐disodioethanes.

et al. 2011

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Reducing versus Basic Properties of 1,2-Diaryl-1,2-disodioethanes. -A particularly mild approach to the synthesis of α-substituted arylacetic acids (III) and (V) is presented, involving title diaryldisodioethanes (NDPE or NTPE) as base at room temperature. For o-halogenated arylacetic acids like (IV), however, the dehalogenated product [cf. (VII)] can be observed as side or main product, depending on the reducing power of the disodioethane reagent. -(AZZENA*, U.; DETTORI, G.; PISANO, L.; PITTALIS, M.; Tetrahedron 67 (2011) 19, 3470-3475, http://dx.

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Reducing versus basic properties of 1,2-diaryl-1,2-disodioethanes

Cited by 8 publications

References 37 publications

Active-alkali metal-promoted reductive cleavage of chlorinated phenols

Active-alkali metal-promoted reductive cleavage of chlorinated phenols

A green solvent approach to the chemistry of 1,2‐diaryl‐1,2‐disodioethanes

ChemInform Abstract: Reducing versus Basic Properties of 1,2‐Diaryl‐1,2‐disodioethanes.

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