A base-stabilized 2-silaallene

Yi Fan Yang; Cechao Foo; Hong Wei Xi; Yongxin Li; Kok Hwa Lim; Cheuk Wai So

doi:10.1021/om301175p

A base-stabilized 2-silaallene

Yi Fan Yang, Cechao Foo, Hong Wei Xi, Yongxin Li, Kok Hwa Lim, Cheuk Wai So^*

^*Corresponding author for this work

Nanyang Technological University

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

12 Citations (Scopus)

Abstract

The reaction of [CH₂(PPh₂S)₂] (1) with 2 equiv of MeLi in Et₂O followed by addition of 0.5 equiv of SiCl ₄ afforded the base-stabilized 2-silaallene [(PPh₂S) ₂CSiC(PPh₂S)₂] (2). It has been characterized by X-ray crystallography, NMR spectroscopy, and theoretical studies. The results show that compound 2 comprises a C^̄-Si²⁺-C ^̄ ylidic skeleton with a negative charge at the C _methanediide atoms and two positive charges at the Si atom. The reaction of 2 with excess PrⁱNCNPrⁱ in refluxing toluene gave the thiophosphinoyl-stabilized silene [(PPh₂S)₂C ^- - Si⁺(NPrⁱ)₂CC(PPh ₂S)₂] (3).

Original language	English
Pages (from-to)	2267-2270
Number of pages	4
Journal	Organometallics
Volume	32
Issue number	7
DOIs	https://doi.org/10.1021/om301175p
Publication status	Published - Apr 8 2013
Externally published	Yes

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "A base-stabilized 2-silaallene",

abstract = "The reaction of [CH2(PPh2S)2] (1) with 2 equiv of MeLi in Et2O followed by addition of 0.5 equiv of SiCl 4 afforded the base-stabilized 2-silaallene [(PPh2S) 2CSiC(PPh2S)2] (2). It has been characterized by X-ray crystallography, NMR spectroscopy, and theoretical studies. The results show that compound 2 comprises a {\=C}-Si2+-C{\= } ylidic skeleton with a negative charge at the C methanediide atoms and two positive charges at the Si atom. The reaction of 2 with excess PriNCNPri in refluxing toluene gave the thiophosphinoyl-stabilized silene [(PPh2S)2C - - Si+(NPri)2CC(PPh 2S)2] (3).",

author = "Yang, {Yi Fan} and Cechao Foo and Xi, {Hong Wei} and Yongxin Li and Lim, {Kok Hwa} and So, {Cheuk Wai}",

year = "2013",

month = apr,

day = "8",

doi = "10.1021/om301175p",

language = "English",

volume = "32",

pages = "2267--2270",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "7",

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TY - JOUR

T1 - A base-stabilized 2-silaallene

AU - Yang, Yi Fan

AU - Foo, Cechao

AU - Xi, Hong Wei

AU - Li, Yongxin

AU - Lim, Kok Hwa

AU - So, Cheuk Wai

PY - 2013/4/8

Y1 - 2013/4/8

N2 - The reaction of [CH2(PPh2S)2] (1) with 2 equiv of MeLi in Et2O followed by addition of 0.5 equiv of SiCl 4 afforded the base-stabilized 2-silaallene [(PPh2S) 2CSiC(PPh2S)2] (2). It has been characterized by X-ray crystallography, NMR spectroscopy, and theoretical studies. The results show that compound 2 comprises a C̄-Si2+-C ̄ ylidic skeleton with a negative charge at the C methanediide atoms and two positive charges at the Si atom. The reaction of 2 with excess PriNCNPri in refluxing toluene gave the thiophosphinoyl-stabilized silene [(PPh2S)2C - - Si+(NPri)2CC(PPh 2S)2] (3).

AB - The reaction of [CH2(PPh2S)2] (1) with 2 equiv of MeLi in Et2O followed by addition of 0.5 equiv of SiCl 4 afforded the base-stabilized 2-silaallene [(PPh2S) 2CSiC(PPh2S)2] (2). It has been characterized by X-ray crystallography, NMR spectroscopy, and theoretical studies. The results show that compound 2 comprises a C̄-Si2+-C ̄ ylidic skeleton with a negative charge at the C methanediide atoms and two positive charges at the Si atom. The reaction of 2 with excess PriNCNPri in refluxing toluene gave the thiophosphinoyl-stabilized silene [(PPh2S)2C - - Si+(NPri)2CC(PPh 2S)2] (3).

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A base-stabilized 2-silaallene

Abstract

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