Journal of Organometallic Chemistry p. 116 - 126 (2000)
Update date:2022-08-18
Topics:
Furukawa, Naomichi
Kobayashi, Kenji
Sato, Soichi
Intramolecular (transannular) and intermolecular through-space interactions between chalcogen atoms have been described. This account includes the following three topics. (1) Various types of bis-chalcogenides and their mono-oxides, which have the two chalcogen atoms in close proximity in a molecule, give the dichalcogena dications upon the oxidation with two equivalents of NOBF4 or treatment with one equivalent of triflic anhydride (Tf2O). The stability of the dichalcogena dications increases in the order S < Se < Te. The dichalcogena dications with flexible scaffolds cause dealkylation via an SN1 type reaction to form chalcogenachalcogenonium salts and alkyl cations. (2) The reaction of 2,6-bis[(phenylthio- or phenylseleno)methyl]phenyl phenyl telluride or the corresponding Te-oxide with NOBF4 or Tf2O affords the positively-charged hypervalent species, dicationic telluranes. Dicationic telluranes can be prepared by the remote oxidation through π-conjugation. The stable sulfenium cation can be isolated by taking advantage of 2,6-bis[(dimethylamino)methyl]phenyl ligand. (3) The remote oxygen migration and Pummerer reactions of p-bis(methylthio)-aromatic mono-oxides are discussed in light of an intermolecular through-space interaction between sulfur atoms, and a cyclic bis(dithia dication) dimer is proposed as an intermediate.
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