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Molecules 2011, 16(9), 8033-8040; doi:10.3390/molecules16098033
Communication

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

Received: 31 August 2011 / Revised: 8 September 2011 / Accepted: 14 September 2011 / Published: 16 September 2011
(This article belongs to the Special Issue Organosilicon Chemistry)
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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 silole; germole; dianion; group 14 metallole; aromaticity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Hong, J.-H. Synthesis and NMR-Study of the 2,3,4,5-Tetraethylsilole Dianion [SiC4Et4]2−•2[Li]+. Molecules 2011, 16, 8033-8040.

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