- Oxidative coupling of diaryldisulfides by MoCl5 to thianthrenes
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"Chemical Equation Presented" Oxidative C-S coupling: The oxidative coupling reaction of 1,2-diaryldisulfides by using MoCl5 or mixtures thereof with TiCl4 gives fast and efficient access to dibenzo[b,e] [1,4]dithiins such as that depicted (thianthrenes).
- Spurg, Anke,Schnakenburg, Gregor,Waldvogel, Siegfried R.
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scheme or table
p. 13313-13317+13274
(2010/06/15)
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- RADIKALIONEN 89. EINELEKTRONEN-OXIDATIONEN VON DIARYLDISULFIDEN MIT AlCl3/H2CCl2
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The single electron oxidation of 14 alkyl and alkoxy substituted diaryldisulfides by AlCl3/H2CCl2 has been investigated by ESR/ENDOR spectroscopy.The radical cations observed prove the following skeletal rearrangements: Those with ring hydrogens in ortho positions to the disulfide bridge preferentially form thianthrene derivatives.The isomeric dinaphthyl disulfides react differently, the 2,2'-isomer yielding the dibenzothianthrene radical cation and the 1,1'-isomer the well-known naphthalene-1,8-disulfide radical cation.For all diaryl disulfides with completely alkyl- or methoxy-blocked ortho positions, oxidative desulfuration is observed.As substantiated by additional (2)D and (33)S isotope marking, the bis(2,5-dimethoxyphenyl)disulfide reacts both to the corresponding thianthrene derivative as well as via desulfuration to the radical cation of the monosulfide.Accompanying cyclovoltammetric and photoelectron spectroscopic measurements prove that all ESR spectroscopically detected radical cations result from compounds Ar-S-Ar, Ar-SS-Ar and Ar(S)2Ar with rather low oxidation or ionisation potentials and thus suggest that each the most easily oxidized paramagnetic species is observed in the rather complex product mixtures, which form on AlCl3/H2CCl2 oxidation of diaryldisulfides. Key words: Diaryl disulfides; one-electron oxidation; radical cations; ESR/ENDOR spectra.
- Bock, Hans,Rittmeyer, Peter
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p. 261 - 292
(2007/10/02)
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- Stacking Structure with Trimolecular Units of Donor-Acceptor-Donor in a Charge-transfer Complex of Dinaphtho-1,4-dithiin with Tetracyanoquinodimethane
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Dinaphtho-1,4-dithiin (DND) was prepared as an electron-donor species and upon reaction with the electron-acceptor species 7,7,8,8-tetracyanoquinodimethane (TCNQ) was found to form a charge-transfer complex with a donor:acceptor ratio of 2:1.The crystal and molecular structure of this complex has been determined.The molecules are arranged in a mixed stack composed of the trimolecular donor-acceptor-donor units, which are further linked by donor-donor overlap.The donor molecules are folded along the S-S axis with a dihedral angle of 140.6 deg.
- Kobayashi, Keiji,Takahashi, Miyuki,Kobayashi, Hayao
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p. 427 - 430
(2007/10/02)
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