Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes

Naoki Asao; Hisamitsu Tomeba; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2004.11.048

Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes

Naoki Asao, Hisamitsu Tomeba, Yoshinori Yamamoto

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

12 Citations (Scopus)

Abstract

The HfCl ₄ catalyzed polymerization of allyl(4-ethynylphenyl) dimethylsilane (1a) proceeded smoothly to give poly[dimethyl-(1,4-pentadienyl) phenylsilane] (2a), and the HfCl ₄ catalyzed reaction of 1-allyl-2-(4-ethynyphenyl)-1,1,2,2-tetramethyldisilane (1b) afforded poly[1,1,2,2-tetramethyl-1-(1,4-pentadienyl)-2-phenyldisilane] (2b). These polymerization reactions proceeded via the stereoselective trans-allylsilylation of the 4-ethynyl group attached to the aromatic ring.

Original language	English
Pages (from-to)	27-30
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.048
Publication status	Published - 2005 Jan 3

Keywords

Allylsilylation
Carbometallation
Hafnium chloride
Lewis-acid catalyst
Organosilicon polymer
σ-π Conjugation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.11.048

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title = "Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes",

abstract = "The HfCl 4 catalyzed polymerization of allyl(4-ethynylphenyl) dimethylsilane (1a) proceeded smoothly to give poly[dimethyl-(1,4-pentadienyl) phenylsilane] (2a), and the HfCl 4 catalyzed reaction of 1-allyl-2-(4-ethynyphenyl)-1,1,2,2-tetramethyldisilane (1b) afforded poly[1,1,2,2-tetramethyl-1-(1,4-pentadienyl)-2-phenyldisilane] (2b). These polymerization reactions proceeded via the stereoselective trans-allylsilylation of the 4-ethynyl group attached to the aromatic ring.",

keywords = "Allylsilylation, Carbometallation, Hafnium chloride, Lewis-acid catalyst, Organosilicon polymer, σ-π Conjugation",

author = "Naoki Asao and Hisamitsu Tomeba and Yoshinori Yamamoto",

year = "2005",

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journal = "Tetrahedron Letters",

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T1 - Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes

AU - Asao, Naoki

AU - Tomeba, Hisamitsu

AU - Yamamoto, Yoshinori

PY - 2005/1/3

Y1 - 2005/1/3

N2 - The HfCl 4 catalyzed polymerization of allyl(4-ethynylphenyl) dimethylsilane (1a) proceeded smoothly to give poly[dimethyl-(1,4-pentadienyl) phenylsilane] (2a), and the HfCl 4 catalyzed reaction of 1-allyl-2-(4-ethynyphenyl)-1,1,2,2-tetramethyldisilane (1b) afforded poly[1,1,2,2-tetramethyl-1-(1,4-pentadienyl)-2-phenyldisilane] (2b). These polymerization reactions proceeded via the stereoselective trans-allylsilylation of the 4-ethynyl group attached to the aromatic ring.

AB - The HfCl 4 catalyzed polymerization of allyl(4-ethynylphenyl) dimethylsilane (1a) proceeded smoothly to give poly[dimethyl-(1,4-pentadienyl) phenylsilane] (2a), and the HfCl 4 catalyzed reaction of 1-allyl-2-(4-ethynyphenyl)-1,1,2,2-tetramethyldisilane (1b) afforded poly[1,1,2,2-tetramethyl-1-(1,4-pentadienyl)-2-phenyldisilane] (2b). These polymerization reactions proceeded via the stereoselective trans-allylsilylation of the 4-ethynyl group attached to the aromatic ring.

KW - Allylsilylation

KW - Carbometallation

KW - Hafnium chloride

KW - Lewis-acid catalyst

KW - Organosilicon polymer

KW - σ-π Conjugation

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DO - 10.1016/j.tetlet.2004.11.048

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JO - Tetrahedron Letters

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Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes

Abstract

Keywords

ASJC Scopus subject areas

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