Synthesis of organofunctional silicon hydride halides from methylchlorosilane

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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 languageEnglish
Pages (from-to)6364-6366
Number of pages3
JournalOrganometallics
Volume27
Issue number23
DOIs
Publication statusPublished - Dec 8 2008

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Silanes
hydrides
halides
Chlorides
methylidyne
silicon
synthesis
Hydrides
chlorides
dihydrides
dichlorides
reagents
cupric chloride

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Synthesis of organofunctional silicon hydride halides from methylchlorosilane. / Missaghi, Michael N.; Downing, Christopher M.; Kung, Mayfair C.; Kung, Harold H.

In: Organometallics, Vol. 27, No. 23, 08.12.2008, p. 6364-6366.

Research output: Contribution to journalArticle

Missaghi, Michael N. ; Downing, Christopher M. ; Kung, Mayfair C. ; Kung, Harold H. / Synthesis of organofunctional silicon hydride halides from methylchlorosilane. In: Organometallics. 2008 ; Vol. 27, No. 23. pp. 6364-6366.
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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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