Synthesis and NMR-Study of the 2,3,4,5-Tetraethylsilole Dianion [SiC4Et4]2−•2[Li]+

Abstract

The previously unknown silole dianion [SiC4Et4]2−•2[Li]+ (3) was prepared by the sonication of 1,1-dichloro-2,3,4,5-tetraethyl-1-silacyclopentadiene [Cl2SiC4Et4, 2] with more than four equivalent of lithium in THF. 1H-, 13C-, and 29Si-NMR data of 3 are compared with those of the reported silole dianion [SiC4Ph4]2−. Trapping of 3 with trimethylchlorosilane gave 1,1-bis(trimethylsilyl)-2,3,4,5-tetraethyl-1-silacyclopentadiene [(Me3Si)2SiC4Et4, 4] in high yield. The silole of 2 was synthesized in high yield in three steps by a modified procedure using Cp2ZrCl2 via Cp2ZrC4Et4 and 1,4-dibromo-1,2,3,4-tetraethyl-1,3-butadiene.

Keywords

• silole
• germole
• dianion
• group 14 metallole
• aromaticity