Platinum-catalyzed Wacker oxidation of alkenes utilizing cis-Pt(Cl) 2(TPPTS) 2 (TPPTS = P(m-C 6H 4SO 3Na) 3)

Derrik S. Helfer; Jim D. Atwood

doi:10.1021/om030500b

Platinum-catalyzed Wacker oxidation of alkenes utilizing cis-Pt(Cl) ₂(TPPTS) ₂ (TPPTS = P(m-C ₆H ₄SO ₃Na) ₃)

Derrik S. Helfer
, Jim D. Atwood

Chemistry

SUNY Buffalo

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

21 Scopus citations

Abstract

Reactions of alkenes (ethylene, propene, and 1-hexene) with water in the presence of cis-Pt(Cl) ₂(TPPTS)2 (TPPTS = P(m-C ₆H ₄SO ₃Na) ₃) produces stoichiometrically the Wacker oxidation product (acetaldehyde, acetone, and 2-hexanone, respectively) and trans-Pt(Cl)-(H)(TPPTS) ₂. The presence of the phosphine ligands provides stability to the hydride complex such that decomposition to the metal is prevented. For C ₂H ₄ the final product is trans-Pt-(Cl)(C ₂H ₅)(TPPTS) ₂. These reactions are fully consistent with the PdCl ₄ ^2- oxidation of alkenes. At higher temperatures, however, C ₂H ₄ is catalytically oxidized to CH ₃CHO in a mechanism that appears to be different. At 95°C, 90 turnovers are observed.

Original language	English
Pages (from-to)	2412-2420
Number of pages	9
Journal	Organometallics
Volume	23
Issue number	10
DOIs	https://doi.org/10.1021/om030500b
State	Published - May 10 2004

Access to Document

10.1021/om030500b

Cite this

@article{770a871d985b41bc81e70b813d56c7dc,

title = "Platinum-catalyzed Wacker oxidation of alkenes utilizing cis-Pt(Cl) 2(TPPTS) 2 (TPPTS = P(m-C 6H 4SO 3Na) 3)",

abstract = "Reactions of alkenes (ethylene, propene, and 1-hexene) with water in the presence of cis-Pt(Cl) 2(TPPTS)2 (TPPTS = P(m-C 6H 4SO 3Na) 3) produces stoichiometrically the Wacker oxidation product (acetaldehyde, acetone, and 2-hexanone, respectively) and trans-Pt(Cl)-(H)(TPPTS) 2. The presence of the phosphine ligands provides stability to the hydride complex such that decomposition to the metal is prevented. For C 2H 4 the final product is trans-Pt-(Cl)(C 2H 5)(TPPTS) 2. These reactions are fully consistent with the PdCl 4 2- oxidation of alkenes. At higher temperatures, however, C 2H 4 is catalytically oxidized to CH 3CHO in a mechanism that appears to be different. At 95°C, 90 turnovers are observed.",

author = "Helfer, \{Derrik S.\} and Atwood, \{Jim D.\}",

year = "2004",

month = may,

day = "10",

doi = "10.1021/om030500b",

language = "English",

volume = "23",

pages = "2412--2420",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Platinum-catalyzed Wacker oxidation of alkenes utilizing cis-Pt(Cl) 2(TPPTS) 2 (TPPTS = P(m-C 6H 4SO 3Na) 3)

AU - Helfer, Derrik S.

AU - Atwood, Jim D.

PY - 2004/5/10

Y1 - 2004/5/10

N2 - Reactions of alkenes (ethylene, propene, and 1-hexene) with water in the presence of cis-Pt(Cl) 2(TPPTS)2 (TPPTS = P(m-C 6H 4SO 3Na) 3) produces stoichiometrically the Wacker oxidation product (acetaldehyde, acetone, and 2-hexanone, respectively) and trans-Pt(Cl)-(H)(TPPTS) 2. The presence of the phosphine ligands provides stability to the hydride complex such that decomposition to the metal is prevented. For C 2H 4 the final product is trans-Pt-(Cl)(C 2H 5)(TPPTS) 2. These reactions are fully consistent with the PdCl 4 2- oxidation of alkenes. At higher temperatures, however, C 2H 4 is catalytically oxidized to CH 3CHO in a mechanism that appears to be different. At 95°C, 90 turnovers are observed.

AB - Reactions of alkenes (ethylene, propene, and 1-hexene) with water in the presence of cis-Pt(Cl) 2(TPPTS)2 (TPPTS = P(m-C 6H 4SO 3Na) 3) produces stoichiometrically the Wacker oxidation product (acetaldehyde, acetone, and 2-hexanone, respectively) and trans-Pt(Cl)-(H)(TPPTS) 2. The presence of the phosphine ligands provides stability to the hydride complex such that decomposition to the metal is prevented. For C 2H 4 the final product is trans-Pt-(Cl)(C 2H 5)(TPPTS) 2. These reactions are fully consistent with the PdCl 4 2- oxidation of alkenes. At higher temperatures, however, C 2H 4 is catalytically oxidized to CH 3CHO in a mechanism that appears to be different. At 95°C, 90 turnovers are observed.

UR - https://www.scopus.com/pages/publications/2542455652

U2 - 10.1021/om030500b

DO - 10.1021/om030500b

M3 - Article

AN - SCOPUS:2542455652

SN - 0276-7333

VL - 23

SP - 2412

EP - 2420

JO - Organometallics

JF - Organometallics

IS - 10

ER -

Platinum-catalyzed Wacker oxidation of alkenes utilizing cis-Pt(Cl) ₂(TPPTS) ₂ (TPPTS = P(m-C ₆H ₄SO ₃Na) ₃)

Abstract

Access to Document

Other files and links

Fingerprint

Cite this