Oxidation of tris(2,4,6-triisopropylphenyl)phosphine and arsine

Shigeru Sasaki; Katsuhide Sutoh; Yusuke Shimizu; Kiyotoshi Kato; Masaaki Yoshifuji

doi:10.1016/j.tetlet.2013.11.004

Oxidation of tris(2,4,6-triisopropylphenyl)phosphine and arsine

Shigeru Sasaki, Katsuhide Sutoh, Yusuke Shimizu, Kiyotoshi Kato, Masaaki Yoshifuji

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

A reaction of the radical cation of tris(2,4,6-triisopropylphenyl)phosphine with oxygen gave a phosphonium salt resulting from the introduction of the oxygen atom to the phosphorus and the formation of a five membered ring by participation of the ortho isopropyl group. On the other hand, oxidation of the phosphine with mCPBA afforded the corresponding phosphine oxide. X-ray crystallography showed that the CPC bond angles and the PC bond lengths of the phosphine oxide are similar to those of the corresponding phosphine. The corresponding arsine underwent analogous reactions to afford the arsonium salt and the arsine oxide.

Original language	English
Pages (from-to)	322-325
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2013.11.004
Publication status	Published - 2014 Jan 8

Keywords

Oxidation
Oxygen
Phosphine oxide
Radical cation
Triarylarsine
Triarylphosphine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2013.11.004

Cite this

@article{e60ae5fc03824db881aa8b363a699429,

title = "Oxidation of tris(2,4,6-triisopropylphenyl)phosphine and arsine",

abstract = "A reaction of the radical cation of tris(2,4,6-triisopropylphenyl)phosphine with oxygen gave a phosphonium salt resulting from the introduction of the oxygen atom to the phosphorus and the formation of a five membered ring by participation of the ortho isopropyl group. On the other hand, oxidation of the phosphine with mCPBA afforded the corresponding phosphine oxide. X-ray crystallography showed that the CPC bond angles and the PC bond lengths of the phosphine oxide are similar to those of the corresponding phosphine. The corresponding arsine underwent analogous reactions to afford the arsonium salt and the arsine oxide.",

keywords = "Oxidation, Oxygen, Phosphine oxide, Radical cation, Triarylarsine, Triarylphosphine",

author = "Shigeru Sasaki and Katsuhide Sutoh and Yusuke Shimizu and Kiyotoshi Kato and Masaaki Yoshifuji",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant numbers 22605001 , 17310063 , 15550025 . We thank Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, for performing mass spectra and elemental analysis. ",

year = "2014",

month = jan,

day = "8",

doi = "10.1016/j.tetlet.2013.11.004",

language = "English",

volume = "55",

pages = "322--325",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "2",

}

TY - JOUR

T1 - Oxidation of tris(2,4,6-triisopropylphenyl)phosphine and arsine

AU - Sasaki, Shigeru

AU - Sutoh, Katsuhide

AU - Shimizu, Yusuke

AU - Kato, Kiyotoshi

AU - Yoshifuji, Masaaki

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant numbers 22605001 , 17310063 , 15550025 . We thank Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, for performing mass spectra and elemental analysis.

PY - 2014/1/8

Y1 - 2014/1/8

N2 - A reaction of the radical cation of tris(2,4,6-triisopropylphenyl)phosphine with oxygen gave a phosphonium salt resulting from the introduction of the oxygen atom to the phosphorus and the formation of a five membered ring by participation of the ortho isopropyl group. On the other hand, oxidation of the phosphine with mCPBA afforded the corresponding phosphine oxide. X-ray crystallography showed that the CPC bond angles and the PC bond lengths of the phosphine oxide are similar to those of the corresponding phosphine. The corresponding arsine underwent analogous reactions to afford the arsonium salt and the arsine oxide.

AB - A reaction of the radical cation of tris(2,4,6-triisopropylphenyl)phosphine with oxygen gave a phosphonium salt resulting from the introduction of the oxygen atom to the phosphorus and the formation of a five membered ring by participation of the ortho isopropyl group. On the other hand, oxidation of the phosphine with mCPBA afforded the corresponding phosphine oxide. X-ray crystallography showed that the CPC bond angles and the PC bond lengths of the phosphine oxide are similar to those of the corresponding phosphine. The corresponding arsine underwent analogous reactions to afford the arsonium salt and the arsine oxide.

KW - Oxidation

KW - Oxygen

KW - Phosphine oxide

KW - Radical cation

KW - Triarylarsine

KW - Triarylphosphine

UR - http://www.scopus.com/inward/record.url?scp=84890798705&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84890798705&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.11.004

DO - 10.1016/j.tetlet.2013.11.004

M3 - Article

AN - SCOPUS:84890798705

SN - 0040-4039

VL - 55

SP - 322

EP - 325

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

Oxidation of tris(2,4,6-triisopropylphenyl)phosphine and arsine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this