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Synthetic pathways to disilylmethane, H 3 SiCH 2 SiH 3 , and methyldisilane, CH 3 SiH 2 SiH 3
Author(s) -
Zech Joachim,
Schmidbaur Hubert
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901231102
Subject(s) - chemistry , phenylsilane , tetrahydrofuran , silylation , medicinal chemistry , alkylation , catalysis , methyllithium , hydrogen bromide , bromide , diethyl ether , organic chemistry , bromine , solvent
Disilylmethane is available in a four‐step synthesis starting with phenylsilane. This is converted into chlorophenylsilane by HCl/AlCl 3 . The reaction of PhSiH 2 Cl and dibromomethane with magnesium in tetrahydrofuran affords bis(phenylsilyl)‐methane, which yields bis(bromosilyl)methane by treatment with anhydrous hydrogen bromide. (BrH 2 Si) 2 CH 2 is converted into disilylmethane by reduction with LiAlH 4 in a two‐phase system using a phase‐transfer catalyst. ‐ Methyldisilane is available by alkylation of a monohalodisilane, XSi 2 H 5 (X Cl, Br), with methyllithium in a high‐boiling ether or by silylation of bromomethylsilane with silylpotassium. Due to secondary silylation reactions the overall yields of methyldisilane are low in all cases.