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Molecules 2013, 18(9), 10568-10579; doi:10.3390/molecules180910568
Article

Synthesis and NMR-Study of 1-Trimethylsilyl Substituted Silole Anion [Ph4C4Si(SiMe3)]•[Li]+ and 3-Silolenide 2,5-carbodianions {[Ph4C4Si(n-Bu)2]2•2[Li]+, [Ph4C4Si(t-Bu)2]2•2[Li]+} via Silole Dianion [Ph4C4Si]2•2[Li]+

Department of Nanopolymer Material Engineering, Pai Chai University, 155-40 Baejae-ro (Doma-Dong), Seo-Gu, Daejon 302-735, Korea Dedicated to Professor Wan-Chul Joo on the occasion of his 89th birthday.
Received: 24 July 2013 / Revised: 21 August 2013 / Accepted: 22 August 2013 / Published: 30 August 2013
(This article belongs to the Section Molecular Diversity)
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Abstract

1-Trimethylsilyl, 1-R (R = Me, Et, i-Bu)-2,3,4,5-tetraphenyl-1-silacyclopentadiene [Ph4C4Si(SiMe3)R] are synthesized from the reaction of 1-trimethylsilyl,1-lithio-2,3,4,5-tetraphenyl-1-silacyclopentadienide anion [Ph4C4SiMe3]•[Li]+ (3) with methyl iodide, ethyl iodide, and i-butyl bromide. The versatile intermediate 3 is prepared by hemisilylation of the silole dianion [Ph4C4Si]−2•2[Li]+ (2) with trimethylsilyl chloride and characterized by 1H-, 13C-, and 29Si-NMR spectroscopy. 1,1-bis(R)-2,3,4,5-tetraphenyl-1-silacyclopentadiene [Ph4C4SiR2] {R = n-Bu (7); t-Bu (8)} are synthesized from the reaction of 2 with n-butyl bromide and t-butyl bromide. Reduction of 7 and 8 with lithium under sonication gives the respective 3-silolenide 2,5-carbodianions {[Ph4C4Si(n-Bu)2]−2•2[Li]+ (10) and [Ph4C4Si(t-Bu)2]−2•2[Li]+ (11)}, which are characterized by 1H-, 13C-, and 29Si-NMR spectroscopy. Polarization of phenyl groups in 3 is compared with those of silole anion/dianion, germole anion/dianion, and 3-silolenide 2,5-carbodianions 10 and 11.
Keywords: silacyclopentadiene; silole; anion; dianion; silyation; 3-silolenide; aromaticity; NMR silacyclopentadiene; silole; anion; dianion; silyation; 3-silolenide; aromaticity; NMR
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Hong, J.-H. Synthesis and NMR-Study of 1-Trimethylsilyl Substituted Silole Anion [Ph4C4Si(SiMe3)]•[Li]+ and 3-Silolenide 2,5-carbodianions {[Ph4C4Si(n-Bu)2]2•2[Li]+, [Ph4C4Si(t-Bu)2]2•2[Li]+} via Silole Dianion [Ph4C4Si]2•2[Li]+. Molecules 2013, 18, 10568-10579.

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