TY - JOUR
T1 - Synthesis of organofunctional silicon hydride halides from methylchlorosilane
AU - Missaghi, Michael N.
AU - Downing, Christopher M.
AU - Kung, Mayfair
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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U2 - 10.1021/om8002625
DO - 10.1021/om8002625
M3 - Article
AN - SCOPUS:57849164152
VL - 27
SP - 6364
EP - 6366
JO - Organometallics
JF - Organometallics
SN - 0276-7333
IS - 23
ER -