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|Section2= |Section3= }} Bis(trimethylsilyl)acetylene (BTMSA) is an organosilicon compound with the formula C2(Si(CH3)3)2. It is a colorless liquid that is soluble in organic solvents. This compound is used as a surrogate for acetylene. BTMSA is prepared by treating acetylene with butyl lithium followed by addition of chlorotrimethylsilane:〔Holmes, A.; Sporikou, C.; Org. Synth. 1993, Coll. Vol. 8, 606.〕〔Walton, D. R. M.; Waugh, F., J. Organomet. Chem. 1972, 37, 45. 〕 :Li2C2 + 2 (CH3)3SiCl → ()2C2 + 2 LiCl == Applications == BTMSA is used as a nucleophile in Friedel-Crafts type acylations and alkylations and a precursor to lithium trimethylsilylacetylide. The TMS groups can be removed with tetra-n-butylammonium fluoride (TBAF) and replaced with protons. BTMSA is also a useful reagent in cycloaddition reactions. Illustrating its versatility, BTMSA was used in a concise total synthesis of (±)-estrone.〔Curtain, M. L.; Wang, C. Bis(trimethylsilyl) acetylene. e-EROS.〕 A key step in this synthesis was the formation of the steroidal skeleton, catalyzed by CpCo(CO)2. BTMSA also serves as a ligand in organometallic chemistry. For example, it forms stable adducts with metallocenes.〔Rosenthal, U.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A. Organometallics 2003, 22, 884. 〕 : Cp2TiCl2 + Mg + Me3SiC≡CSiMe3 → Cp2Ti() + MgCl2 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Bis(trimethylsilyl)acetylene」の詳細全文を読む スポンサード リンク
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