Hexachlorobutadiene → 1,4-Bis(dimethylaminodimethylsilyl)butadiyne

Participants

Reaction Conditions

Reaction Steps

Synthesis of 1,4-bis(dimethylaminodimethylsilyl)butadiyne—A flame dried 250 mL Schlenk flask containing diethyl ether (20 mL) was cooled to −78° C. and n-butyl lithium (20 mL of 2.4 M in hexane, 48.0 mmol) was added by syringe. After several minutes, hexachlorobutadiene (1.88 mL, 12.0 mmol) was added drop wise via syringe over a 10 minute period. After completion of addition, the cold bath was removed and the mixture stirred at room temperature for 3 hours. The resulting 1,4-dilithio-1,3-butadiyne was used without further purification. The flask was then recooled to −78° C. and dimethylaminodimethylchlorosilane (3.6 mL, 24 mmol) was added by syringe. The flask was removed from the cold bath and the reaction mixture stirred at room temperature for 16 hours. At this time, 1H NMR analysis indicated complete disappearance of dimethylaminodimethylchlorosilane and formation of 1,4-bis(dimethylaminodimethylsilyl)butadiyne 206. Diethyl ether was removed in vacuo, and the mixture taken up in a minimum amount of pentane and filtered. Pentane was removed in vacuo to give 2.91 g (96%) of 1,4-bis(dimethylaminodimethylsilyl)butadiyne 206 as a viscous red liquid. IR (cm−1) 2074 (s), (—C≡C—C≡C—). 1H NMR (ppm) 2.44 (s), (N(CH3)2), 0.20 (s), (Si(CH3)2). 13C NMR 87.6, 84.4, (—C≡C—C≡C—) 37.7, (N(CH3)2), −1.2, (Si(CH3)2).

Provenance & Evidence