Aromatic and Alkaromatic Chlorocarbons

Ballester, Manuel; Olivella, Santiago

doi:10.1007/978-1-4684-2097-5_1

Cited by 7 publications

(4 citation statements)

References 281 publications

(522 reference statements)

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“…AlCl 3 /CH 2 Cl 2 converts perchloro-4,4‘-diphenyltriphenylmethyl ( PDTM • ) and perchloro-4,4‘,4‘ ‘-triphenyltriphenylmethyl ( PTTM • ) radicals16a into the corresponding carbocations, as reagent AlCl 3 /SO 2 Cl 2 does 16b …”

Section: Resultsmentioning

confidence: 99%

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

et al. 2003

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A solution of AlCl(3) in CH(2)Cl(2) reacts slowly, at room temperature, with perchlorotriphenylmethyl radical (PTM(*)), an inert carbon free radical, to give perchlorotriphenylmethyl cation (PTM(+)) quantitatively. However, by gradual addition of CH(2)Cl(2) into the resulting solution a point is reached where the PTM(+) reverts to PTM(*) instantaneously and quantitatively. A mechanism for this exceptional phenomenon is suggested. Some PTM(+) reactions, namely hydrolysis yielding quinonoid species and single-electron transfers with hydride ion donors, are reported and discussed.

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Section: Resultsmentioning

confidence: 99%

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

et al. 2003

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“…As the last attempt to synthesize the polytriarylmethane 8 , the precursor of the second generation of series III, we performed an exhaustive perchlorination of 11 using the BMC reagent . This reagent is a powerful chlorinating agent that was extensively used in the perchlorination of a great number of triarylmethanes . However, this was the first time in which such a chlorinating agent has been used with a molecule such as 11 with a large structural complexity.…”

Section: Resultsmentioning

confidence: 99%

Drawbacks Arising from the High Steric Congestion in the Synthesis of New Dendritic Polyalkylaromatic Polyradicals

et al. 1997

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The synthesis of the highly strained tris(R,R-bis(pentachlorophenyl)-2,4,5,6-tetrachlorotolyl)methane (8), which is the precursor of the first generation of the polyradical series III, has been achieved by exhaustive chlorination of compound 11. Stepwise divergent synthesis, by successive FriedelCrafts reactions, of the precursors of dendritic series II and III was not possible since the limit generation was reached in the earlier synthetic steps due to high steric congestion. Several polyradical mixtures derived from 8 have also been prepared, being stable under ambient conditions. The formation, electrochemistry, and magnetic properties of these polyradical species are discussed. The steric hindrance of highly chlorinated hydrocarbon 8 prevents the formation of tetraradical 15.

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“…Steric hindrance about the diphosphinomethane carbon atoms and the σ-donor and π-acceptor properties of the phosphine groups may also contribute to the difficulty of preparing tetra(diphenylphosphino)quinodimethane. A general lack of stability is observed in quinodimethanes when strong electron-withdrawing substituents are not present. − The oxidation of dppx, complexed to transition metal centers, may afford better routes to phosphinoquinodimethanes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the Tetradentate Phosphine α,α,α‘,α‘-Tetrakis(diphenylphosphino)-p-xylene (dppx) and Crystal and Molecular Structure of (CO)₃Fe(dppx)Fe(CO)₃

1997

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The tetradentate phosphine α,α,α‘,α‘-tetrakis(diphenylphosphino)-p-xylene (3, dppx) was prepared in two steps from α,α‘-bis(diphenylphosphino)-p-xylene (1) via the intermediate trisubstituted phosphine α,α,α‘-tris(diphenylphosphino)-p-xylene (2). The ligand, dppx, reacts with Fe2(CO)9 to afford a bridging bischelated complex Fe(CO)3(dppx)Fe(CO)3 (4), which was characterized by X-ray diffraction. Complex 4 crystallized in the monoclinic space group P21/n, a = 11.903(1) Å, b = 15.295(2) Å, c = 15.415(1) Å, β = 96.306(9)°, V = 2789.5(8)Å3, Z = 2, R = 0.072, and R w = 0.079.

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Aromatic and Alkaromatic Chlorocarbons

Cited by 7 publications

References 281 publications

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

Drawbacks Arising from the High Steric Congestion in the Synthesis of New Dendritic Polyalkylaromatic Polyradicals

Synthesis of the Tetradentate Phosphine α,α,α‘,α‘-Tetrakis(diphenylphosphino)-p-xylene (dppx) and Crystal and Molecular Structure of (CO)₃Fe(dppx)Fe(CO)₃

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Aromatic and Alkaromatic Chlorocarbons

Cited by 7 publications

References 281 publications

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

Oxidation of the Perchlorotriphenylmethyl Radical to the Carbocation, and Its Unique Abrupt Reversion

Drawbacks Arising from the High Steric Congestion in the Synthesis of New Dendritic Polyalkylaromatic Polyradicals

Synthesis of the Tetradentate Phosphine α,α,α‘,α‘-Tetrakis(diphenylphosphino)-p-xylene (dppx) and Crystal and Molecular Structure of (CO)3Fe(dppx)Fe(CO)3

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Synthesis of the Tetradentate Phosphine α,α,α‘,α‘-Tetrakis(diphenylphosphino)-p-xylene (dppx) and Crystal and Molecular Structure of (CO)₃Fe(dppx)Fe(CO)₃