Synthesis of organofunctional silicon hydride halides from methylchlorosilane

Michael N. Missaghi; Christopher M. Downing; Mayfair C. Kung; Harold H. Kung

doi:10.1021/om8002625

Synthesis of organofunctional silicon hydride halides from methylchlorosilane

Michael N. Missaghi, Christopher M. Downing, Mayfair C. Kung, Harold H. Kung

Chemical and Biological Engineering

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

11 Scopus citations

Abstract

The organofunctional silicon hydride halides R(CH₃)SiHCl were prepared in high yields from CH₃SiHCl₂, employing CH ₃SiH₂Cl as an intermediate. CH₃SiHCl ₂ was converted to CH₃SiH₂Cl by chloride-hydride redistribution in 41% yield (based on Si-H). The chloride substituent in CH₃SiH₂Cl reacted selectively with the Grignard reagent RMgX to form the corresponding dihydride R(CH ₃)SiH₂, where R = H₂C=CH-, H ₂C=C(CH₃)-, H₂C=CHCH₂-, (CH ₃)₂CH-, H₂C=CHCH₂CH₂-, c-C₅H₉-, PhCH₂-, and p-Cl(C₆H ₄)-. Cl(CH₂)₃(CH₃)SiH₂ was also prepared by reduction of the corresponding dichloride. Monohalogenation of R(CH₃)SiH₂ with CuCl₂/CuI in THF then gave CH₃RSiHCl in 60-88% overall yield (starting from CH ₃SiH₂Cl).

Original language	English (US)
Pages (from-to)	6364-6366
Number of pages	3
Journal	Organometallics
Volume	27
Issue number	23
DOIs	https://doi.org/10.1021/om8002625
State	Published - Dec 8 2008

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Synthesis of organofunctional silicon hydride halides from methylchlorosilane",

abstract = "The organofunctional silicon hydride halides R(CH3)SiHCl were prepared in high yields from CH3SiHCl2, employing CH 3SiH2Cl as an intermediate. CH3SiHCl 2 was converted to CH3SiH2Cl by chloride-hydride redistribution in 41% yield (based on Si-H). The chloride substituent in CH3SiH2Cl reacted selectively with the Grignard reagent RMgX to form the corresponding dihydride R(CH 3)SiH2, where R = H2C=CH-, H 2C=C(CH3)-, H2C=CHCH2-, (CH 3)2CH-, H2C=CHCH2CH2-, c-C5H9-, PhCH2-, and p-Cl(C6H 4)-. Cl(CH2)3(CH3)SiH2 was also prepared by reduction of the corresponding dichloride. Monohalogenation of R(CH3)SiH2 with CuCl2/CuI in THF then gave CH3RSiHCl in 60-88% overall yield (starting from CH 3SiH2Cl).",

author = "Missaghi, {Michael N.} and Downing, {Christopher M.} and Kung, {Mayfair C.} and Kung, {Harold H.}",

year = "2008",

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doi = "10.1021/om8002625",

language = "English (US)",

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journal = "Organometallics",

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T1 - Synthesis of organofunctional silicon hydride halides from methylchlorosilane

AU - Missaghi, Michael N.

AU - Downing, Christopher M.

AU - Kung, Mayfair C.

AU - Kung, Harold H.

PY - 2008/12/8

Y1 - 2008/12/8

N2 - The organofunctional silicon hydride halides R(CH3)SiHCl were prepared in high yields from CH3SiHCl2, employing CH 3SiH2Cl as an intermediate. CH3SiHCl 2 was converted to CH3SiH2Cl by chloride-hydride redistribution in 41% yield (based on Si-H). The chloride substituent in CH3SiH2Cl reacted selectively with the Grignard reagent RMgX to form the corresponding dihydride R(CH 3)SiH2, where R = H2C=CH-, H 2C=C(CH3)-, H2C=CHCH2-, (CH 3)2CH-, H2C=CHCH2CH2-, c-C5H9-, PhCH2-, and p-Cl(C6H 4)-. Cl(CH2)3(CH3)SiH2 was also prepared by reduction of the corresponding dichloride. Monohalogenation of R(CH3)SiH2 with CuCl2/CuI in THF then gave CH3RSiHCl in 60-88% overall yield (starting from CH 3SiH2Cl).

AB - The organofunctional silicon hydride halides R(CH3)SiHCl were prepared in high yields from CH3SiHCl2, employing CH 3SiH2Cl as an intermediate. CH3SiHCl 2 was converted to CH3SiH2Cl by chloride-hydride redistribution in 41% yield (based on Si-H). The chloride substituent in CH3SiH2Cl reacted selectively with the Grignard reagent RMgX to form the corresponding dihydride R(CH 3)SiH2, where R = H2C=CH-, H 2C=C(CH3)-, H2C=CHCH2-, (CH 3)2CH-, H2C=CHCH2CH2-, c-C5H9-, PhCH2-, and p-Cl(C6H 4)-. Cl(CH2)3(CH3)SiH2 was also prepared by reduction of the corresponding dichloride. Monohalogenation of R(CH3)SiH2 with CuCl2/CuI in THF then gave CH3RSiHCl in 60-88% overall yield (starting from CH 3SiH2Cl).

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IS - 23

ER -

Synthesis of organofunctional silicon hydride halides from methylchlorosilane

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