Syntheses and Reactivities of Stable Halosilylenoids, (Tsi)X 2SiLi (Tsi = C(SiMe3)3, X = Br, Cl)

Myong Euy Lee, Hyeon Mo Cho, Young Mook Lim, Jin Kyong Choi, Chang Hee Park, Seong Eun Jeong, Uk Lee

Research output: Contribution to journalArticlepeer-review

70 Citations (Scopus)


Halosilylenoids, stable at room temperature (Tsi)X2SiLi (Tsi = C(SiMe3)3, X = Br, Cl), were synthesized from the reaction of TsiSiX3 with lithium naphthalenide. Bromosilylenoid reacted with tBuOH and MeI both at -78°C and at room temperature to give (Tsi)HSiBr2 and (Tsi)MeSiBr2, respectively, in high yields; this clearly shows its nucleophilicity. In the reaction of bromosilylenoid with methanol, 2-propanol, and 2,3-dimethyl-1,3-butadiene, the corresponding products, (Tsi)HSi(OMe)2, (Tsi)HSi(OiPr)Br, and bromo(Tsi)silacyclopent-3-ene, were obtained in high yields; this demonstrates its amphiphilic property, as if bromosilylene would be trapped. Chlorosilylenoid also exhibited both nucleophilic and amphiphilic properties. The 29Si chemical shifts for (Tsi)Br2SiLi, (Tsi)Br 2SiK, and (Tsi)Cl2SiLi were 106, 70, and 87 ppm, respectively.

Original languageEnglish
Pages (from-to)377-381
Number of pages5
JournalChemistry - A European Journal
Issue number2
Publication statusPublished - 2004 Jan 23

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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