Triphenylphosphine-mediated reduction of electron-deficient propargyl ethers to the allylic ethers

Ming Shan Tsai; U. Narasimha Rao; Jeng Rong Wang; Chung Hao Liang; Ming Chang P. Yeh

doi:10.1002/jccs.200100126

Triphenylphosphine-mediated reduction of electron-deficient propargyl ethers to the allylic ethers

Ming Shan Tsai, U. Narasimha Rao, Jeng Rong Wang, Chung Hao Liang, Ming Chang P. Yeh

Department of Chemistry

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

4 Citations (Scopus)

Abstract

Semihydrogenation of α,β-unsaturated ynoates and -ynones bearing a γ-alkoxy group can be performed using triphenylphosphine and water. α,β-Unsaturated ynoates were reduced to a mixture of cis and trans α,β-unsaturated enoates, whereas, ynones were reduced to trans α,β-unsaturated enones as the only products.

Original language	English
Pages (from-to)	869-876
Number of pages	8
Journal	Journal of the Chinese Chemical Society
Volume	48
Issue number	5
DOIs	https://doi.org/10.1002/jccs.200100126
Publication status	Published - 2001 Jan 1

Keywords

Propargyl ether
Semihydrogenation
Triphenylphosphine
α,β-Unsaturated enoate
α,β-Unsaturated enone
α,β-Unsaturated ynoate
α,β-Unsaturated ynone

ASJC Scopus subject areas

Chemistry(all)

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10.1002/jccs.200100126

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title = "Triphenylphosphine-mediated reduction of electron-deficient propargyl ethers to the allylic ethers",

abstract = "Semihydrogenation of α,β-unsaturated ynoates and -ynones bearing a γ-alkoxy group can be performed using triphenylphosphine and water. α,β-Unsaturated ynoates were reduced to a mixture of cis and trans α,β-unsaturated enoates, whereas, ynones were reduced to trans α,β-unsaturated enones as the only products.",

keywords = "Propargyl ether, Semihydrogenation, Triphenylphosphine, α,β-Unsaturated enoate, α,β-Unsaturated enone, α,β-Unsaturated ynoate, α,β-Unsaturated ynone",

author = "Tsai, {Ming Shan} and Rao, {U. Narasimha} and Wang, {Jeng Rong} and Liang, {Chung Hao} and Yeh, {Ming Chang P.}",

year = "2001",

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language = "English",

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T1 - Triphenylphosphine-mediated reduction of electron-deficient propargyl ethers to the allylic ethers

AU - Tsai, Ming Shan

AU - Rao, U. Narasimha

AU - Wang, Jeng Rong

AU - Liang, Chung Hao

AU - Yeh, Ming Chang P.

PY - 2001/1/1

Y1 - 2001/1/1

N2 - Semihydrogenation of α,β-unsaturated ynoates and -ynones bearing a γ-alkoxy group can be performed using triphenylphosphine and water. α,β-Unsaturated ynoates were reduced to a mixture of cis and trans α,β-unsaturated enoates, whereas, ynones were reduced to trans α,β-unsaturated enones as the only products.

AB - Semihydrogenation of α,β-unsaturated ynoates and -ynones bearing a γ-alkoxy group can be performed using triphenylphosphine and water. α,β-Unsaturated ynoates were reduced to a mixture of cis and trans α,β-unsaturated enoates, whereas, ynones were reduced to trans α,β-unsaturated enones as the only products.

KW - Propargyl ether

KW - Semihydrogenation

KW - Triphenylphosphine

KW - α,β-Unsaturated enoate

KW - α,β-Unsaturated enone

KW - α,β-Unsaturated ynoate

KW - α,β-Unsaturated ynone

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DO - 10.1002/jccs.200100126

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EP - 876

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JF - Journal of the Chinese Chemical Society

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