Next Article in Journal
In Vitro Delivery and Controlled Release of Doxorubicin for Targeting Osteosarcoma Bone Cancer
Previous Article in Journal
Ensemble-Based Interpretations of NMR Structural Data to Describe Protein Internal Dynamics
Article Menu

Export Article

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

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)
View Full-Text   |   Download PDF [291 KB, uploaded 18 June 2014]   |  

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. View Full-Text
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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top