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 journalArticle

66 Citations (Scopus)

Abstract

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
Volume10
Issue number2
DOIs
Publication statusPublished - 2004 Jan 23

Fingerprint

2-Propanol
Chemical shift
Propanol
Butadiene
Lithium
Methanol
Temperature
2,3-dimethyl-1,3-butadiene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Lee, Myong Euy ; Cho, Hyeon Mo ; Lim, Young Mook ; Choi, Jin Kyong ; Park, Chang Hee ; Jeong, Seong Eun ; Lee, Uk. / Syntheses and Reactivities of Stable Halosilylenoids, (Tsi)X 2SiLi (Tsi = C(SiMe3)3, X = Br, Cl). In: Chemistry - A European Journal. 2004 ; Vol. 10, No. 2. pp. 377-381.
@article{5b000004125d435b9d6730eba01216ee,
title = "Syntheses and Reactivities of Stable Halosilylenoids, (Tsi)X 2SiLi (Tsi = C(SiMe3)3, X = Br, Cl)",
abstract = "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.",
author = "Lee, {Myong Euy} and Cho, {Hyeon Mo} and Lim, {Young Mook} and Choi, {Jin Kyong} and Park, {Chang Hee} and Jeong, {Seong Eun} and Uk Lee",
year = "2004",
month = "1",
day = "23",
doi = "10.1002/chem.200305151",
language = "English",
volume = "10",
pages = "377--381",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "2",

}

Syntheses and Reactivities of Stable Halosilylenoids, (Tsi)X 2SiLi (Tsi = C(SiMe3)3, X = Br, Cl). / Lee, Myong Euy; Cho, Hyeon Mo; Lim, Young Mook; Choi, Jin Kyong; Park, Chang Hee; Jeong, Seong Eun; Lee, Uk.

In: Chemistry - A European Journal, Vol. 10, No. 2, 23.01.2004, p. 377-381.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Syntheses and Reactivities of Stable Halosilylenoids, (Tsi)X 2SiLi (Tsi = C(SiMe3)3, X = Br, Cl)

AU - Lee, Myong Euy

AU - Cho, Hyeon Mo

AU - Lim, Young Mook

AU - Choi, Jin Kyong

AU - Park, Chang Hee

AU - Jeong, Seong Eun

AU - Lee, Uk

PY - 2004/1/23

Y1 - 2004/1/23

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0842303783&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0842303783&partnerID=8YFLogxK

U2 - 10.1002/chem.200305151

DO - 10.1002/chem.200305151

M3 - Article

C2 - 14735506

AN - SCOPUS:0842303783

VL - 10

SP - 377

EP - 381

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 2

ER -