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 journalArticle

20 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

Fingerprint

Oxides
reactivity
oxides
Bearings (structural)
Antimony
Arsenic
antimony
Ketones
aldehydes
Aldehydes
arsenic
ketones
Dimers
Phosphorus
phosphorus
Electrostatics
alcohols
Stabilization
stabilization
dimers

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides. / Matano, Yoshihiro; Nomura, Hazumi; Hisanaga, Teppei; Nakano, Haruyuki; Shiro, Motoo; Imahori, Hiroshi.

In: Organometallics, Vol. 23, No. 23, 08.11.2004, p. 5471-5480.

Research output: Contribution to journalArticle

Matano, Yoshihiro ; Nomura, Hazumi ; Hisanaga, Teppei ; Nakano, Haruyuki ; Shiro, Motoo ; Imahori, Hiroshi. / Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides. In: Organometallics. 2004 ; Vol. 23, No. 23. pp. 5471-5480.
@article{029b1b7e4b3146d08b4d6cb18ea53a50,
title = "Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides",
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.",
author = "Yoshihiro Matano and Hazumi Nomura and Teppei Hisanaga and Haruyuki Nakano and Motoo Shiro and Hiroshi Imahori",
year = "2004",
month = "11",
day = "8",
doi = "10.1021/om0494115",
language = "English",
volume = "23",
pages = "5471--5480",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

T1 - Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides

AU - Matano, Yoshihiro

AU - Nomura, Hazumi

AU - Hisanaga, Teppei

AU - Nakano, Haruyuki

AU - Shiro, Motoo

AU - Imahori, Hiroshi

PY - 2004/11/8

Y1 - 2004/11/8

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=9144232387&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=9144232387&partnerID=8YFLogxK

U2 - 10.1021/om0494115

DO - 10.1021/om0494115

M3 - Article

AN - SCOPUS:9144232387

VL - 23

SP - 5471

EP - 5480

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 23

ER -