Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes

Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates

Soon Hyun Hong, Sang Il Hyun, Il Nam Jung, Won Sik Han, Min Hye Kim, Hoseop Yun, SukWoo Nam, Sang Ook Kang

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Cyclic and linear carbosilanes, (Cl2SiCH2) 2 (2) and Cl2Si(CH2SiCl3) 2 (3), were produced from phosphine-catalized Si-C coupling reactions of bissilylmethanes, HCl2SiCH2SiX1X 2Cl (X1, X2 = Cl (1), X1 = H, X 2 = Cl (7), and X1 = Me, X2 = Cl (8)). The formation of compounds 2 and 3 suggested competing reaction pathways, involving dichlorosilene [CH2=SiCl2] and dichlorosilylene [:SiCl2] intermediates. Each intermediate was either proposed by the product isolation of the trimerized product (3) or confirmed by trapping experiments with 2,3-dimethylbutadiene and methylene chloride.

Original languageEnglish
Pages (from-to)687-691
Number of pages5
JournalOrganometallics
Volume29
Issue number3
DOIs
Publication statusPublished - 2010 Feb 8
Externally publishedYes

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phosphine
Methylene Chloride
phosphines
preparation
products
methylene
isolation
Experiments
trapping
chlorides
carbosilane

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes : Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates. / Hong, Soon Hyun; Hyun, Sang Il; Jung, Il Nam; Han, Won Sik; Kim, Min Hye; Yun, Hoseop; Nam, SukWoo; Kang, Sang Ook.

In: Organometallics, Vol. 29, No. 3, 08.02.2010, p. 687-691.

Research output: Contribution to journalArticle

Hong, Soon Hyun ; Hyun, Sang Il ; Jung, Il Nam ; Han, Won Sik ; Kim, Min Hye ; Yun, Hoseop ; Nam, SukWoo ; Kang, Sang Ook. / Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes : Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates. In: Organometallics. 2010 ; Vol. 29, No. 3. pp. 687-691.
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abstract = "Cyclic and linear carbosilanes, (Cl2SiCH2) 2 (2) and Cl2Si(CH2SiCl3) 2 (3), were produced from phosphine-catalized Si-C coupling reactions of bissilylmethanes, HCl2SiCH2SiX1X 2Cl (X1, X2 = Cl (1), X1 = H, X 2 = Cl (7), and X1 = Me, X2 = Cl (8)). The formation of compounds 2 and 3 suggested competing reaction pathways, involving dichlorosilene [CH2=SiCl2] and dichlorosilylene [:SiCl2] intermediates. Each intermediate was either proposed by the product isolation of the trimerized product (3) or confirmed by trapping experiments with 2,3-dimethylbutadiene and methylene chloride.",
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AU - Hong, Soon Hyun

AU - Hyun, Sang Il

AU - Jung, Il Nam

AU - Han, Won Sik

AU - Kim, Min Hye

AU - Yun, Hoseop

AU - Nam, SukWoo

AU - Kang, Sang Ook

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AB - Cyclic and linear carbosilanes, (Cl2SiCH2) 2 (2) and Cl2Si(CH2SiCl3) 2 (3), were produced from phosphine-catalized Si-C coupling reactions of bissilylmethanes, HCl2SiCH2SiX1X 2Cl (X1, X2 = Cl (1), X1 = H, X 2 = Cl (7), and X1 = Me, X2 = Cl (8)). The formation of compounds 2 and 3 suggested competing reaction pathways, involving dichlorosilene [CH2=SiCl2] and dichlorosilylene [:SiCl2] intermediates. Each intermediate was either proposed by the product isolation of the trimerized product (3) or confirmed by trapping experiments with 2,3-dimethylbutadiene and methylene chloride.

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