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; Suk Woo Nam; Sang Ook Kang

doi:10.1021/om901071k

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, Suk Woo Nam, Sang Ook Kang

GREEN SCHOOL (Graduate School of Energy and Environment)

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

8 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 language	English
Pages (from-to)	687-691
Number of pages	5
Journal	Organometallics
Volume	29
Issue number	3
DOIs	https://doi.org/10.1021/om901071k
Publication status	Published - 2010 Feb 8

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{d14416d7e77e460c96a88fca1fc2b263,

title = "Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes: Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates",

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.",

author = "Hong, {Soon Hyun} and Hyun, {Sang Il} and Jung, {Il Nam} and Han, {Won Sik} and Kim, {Min Hye} and Hoseop Yun and Nam, {Suk Woo} and Kang, {Sang Ook}",

year = "2010",

month = feb,

day = "8",

doi = "10.1021/om901071k",

language = "English",

volume = "29",

pages = "687--691",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "3",

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TY - JOUR

T1 - Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes

T2 - Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates

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, Suk Woo

AU - Kang, Sang Ook

PY - 2010/2/8

Y1 - 2010/2/8

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=76149114609&partnerID=8YFLogxK

U2 - 10.1021/om901071k

DO - 10.1021/om901071k

M3 - Article

AN - SCOPUS:76149114609

SN - 0276-7333

VL - 29

SP - 687

EP - 691

JO - Organometallics

JF - Organometallics

IS - 3

ER -

Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes: Preparation of Cyclic (Cl₂SiCH₂)₂ and Linear Cl ₂Si(CH₂SiCl₃)₂ via Silylene and Silene Intermediates

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