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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

원문정보

초록

영어

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). 13C-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 13C-NMR spectrum are observed.

목차

Abstract
 1. Introduction
 2. Experimental Section
  2.1. General Procedures
  2.2. 1,1-bis(n-butyl)-2,3,4,5-tetraphenyl-1-silacyclopentadiene(3).
  2.3. 1,1-Bis(t-butyl)-2,3,4,5-tetraphenyl-1-silacyclopentadiene(4).
  2.4. NMR Study of the Reduction of (3) and (4) with Lithium in THF-d8.
 3. Results and Discussion
  3.1. Preparation of 1.1-bis(n-butyl/t-butyl)-2,3,4,5-tetraphenyl-silacyclopentadiene
  3.2. Reduction of 1.1-bis(n-butyl/t-butyl)-2,3,4,5-tetraphenyl-silacyclopentadiene and NMR Study of their Reduced Species
  3.3. NMR Study of their Reduced Species (6 and7) of 1.1-bis(n-butyl/t-butyl)-2,3,4,5-tetraphenyl-silacyclopentadiene
  3.4. Inversion of tert-carbanions in (6) and (7)
 4. Conclusions
 Acknowledgments
 References

저자정보

  • Jang-Hwan Hong Department of Nanopolymer Material Engineering, Pai Chai University

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