Journal of Integrative Natural Science (통합자연과학논문집)

The Basic Science Institute Chosun University (조선대학교 기초과학연구원)
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Synthesis of 1,1-Bis(n-butyl, t-butyl)-2,3,4,5-Tetraphenyl-1-Silacyclopentadiene and NMR Study of Their 2,5-Carbodianions

  • Hong, Jang-Hwan (Department of Nanopolymer Material Engineering, Pai Chai University)
  • Received : 2013.06.05
  • Accepted : 2013.06.24
  • Published : 2013.06.30
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Abstract

1,1-Bis(n-butyl)-2,3,4,5-tetraphenyl-1-silacyclopentadiene (3) and 1,1-bis(t-butyl)-2,3,4,5-tetraphenyl-1-silacyclopentadiene (4) are synthesized from the reaction of the versatile silole dianion (2) with n-butyl bromide and t-butyl bromide. Reduction of (3) and (4) with an excess of lithium to give 1,1-bis(n-butyl)-2,5-dilithio-2,3,4,5-tetraphenyl-1-silacyclopenta-3-enide (6) and 1,1-bis(t-butyl)-2,5-dilithio-2,3,4,5-tetraphenyl-1-silacyclopenta-3-enide (7). $^{13}C$-NMR study of two 2,5-carbodianions (6 and 7) shows tert-carbanion at 73.18 and 78.12 ppm respectively. Two bulky tert-butyl groups in (7) increase the inversion barrier at the tert-carbanion, line broadenings of tert-butyl groups in $^1H$ and $^{13}C$-NMR spectrum are observed.

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References

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