Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides

Yoshihiro Matano, Hazumi Nomura, Teppei Hisanaga, Haruyuki Nakano, Motoo Shiro, Hiroshi Imahori

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

A systematic series of triarylbismuthane oxides was prepared in order to disclose their structure and reactivity, which have been compared with those of lighter pnictogen counterparts. X-ray crystallographic analysis of tris(2-methoxyphenyl)bismuthane oxide and tris(2-methoxyphenyl)stibane oxide revealed that they exist as dimers with a flat bis(a-oxo) ring, implying that the polarized Bi+-O- and Sb+-O- bonds aggregate to attain electrostatic stabilization. In sharp contrast to their phosphorus, arsenic, and antimony counterparts, triarylbismuthane oxides are thermally unstable and possess a high oxidizing ability. In particular, the bismuthane oxides bearing ortho-substituted aryl ligands oxidized primary and secondary alcohols to aldehydes and ketones, respectively, with high efficiency under mild conditions.

Original languageEnglish
Pages (from-to)5471-5480
Number of pages10
JournalOrganometallics
Volume23
Issue number23
DOIs
Publication statusPublished - Nov 8 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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