1,3-Bis(triisopropylsilyl)propyne
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1,3-Bis(triisopropylsilyl)propyne. / Rücker, Christoph.
Encyclopedia of Reagents for Organic Synthesis: Band 1. Hrsg. / Leo A. Paquette; S. Denmark. Chichester : John Wiley & Sons Ltd., 1995. S. 583-585.Publikation: Beiträge in Sammelwerken › Lexikonbeiträge › Forschung
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TY - CHAP
T1 - 1,3-Bis(triisopropylsilyl)propyne
AU - Rücker, Christoph
PY - 1995
Y1 - 1995
N2 - C21H44Si2 (MW 352.75)InChI = 1S/C21H44Si2/c1‐16(2)22(17(3)4,18(5)6)14‐13‐15‐23(19(7)8,20(9)10)21(11)12/h16‐21H,14H2,1‐12H3InChIKey = JFDDOGUVACDNTR‐UHFFFAOYSA‐N(precursor of a stereoselective bulky C3 nucleophile, functionalized Peterson reagent1)Alternate Name: 1,3‐bis(TIPS)propyne.Physical Data: bp 130–135 °C/0.08 mmHg; d 0.846 g cm−3.Solubility: both the reagent and its lithio derivative are soluble in ether or THF.Analysis of Reagent Purity: GC at 210 °C on a glass capillary column coated with OV‐17; TLC on silica (hexanes, R f 0.75). 1H NMR (CDCl3, 80 MHz): δ = 1.63 (s, CH2), 1.3–0.9 (m, 2 TIPS).Preparative Method: 1,3‐bis(TIPS)propyne is prepared in quantitative yield by silylation of 3‐Lithio‐1‐triisopropylsilyl‐1‐propyne with Triisopropylsilyl Trifluoromethanesulfonate.2Purification: by distillation or chromatography.Handling, Storage, and Precautions: no special precautions required; the reagent is not changed when stored for several months at ambient temperature. The Li derivative is handled under inert gas using simple syringe equipment.
AB - C21H44Si2 (MW 352.75)InChI = 1S/C21H44Si2/c1‐16(2)22(17(3)4,18(5)6)14‐13‐15‐23(19(7)8,20(9)10)21(11)12/h16‐21H,14H2,1‐12H3InChIKey = JFDDOGUVACDNTR‐UHFFFAOYSA‐N(precursor of a stereoselective bulky C3 nucleophile, functionalized Peterson reagent1)Alternate Name: 1,3‐bis(TIPS)propyne.Physical Data: bp 130–135 °C/0.08 mmHg; d 0.846 g cm−3.Solubility: both the reagent and its lithio derivative are soluble in ether or THF.Analysis of Reagent Purity: GC at 210 °C on a glass capillary column coated with OV‐17; TLC on silica (hexanes, R f 0.75). 1H NMR (CDCl3, 80 MHz): δ = 1.63 (s, CH2), 1.3–0.9 (m, 2 TIPS).Preparative Method: 1,3‐bis(TIPS)propyne is prepared in quantitative yield by silylation of 3‐Lithio‐1‐triisopropylsilyl‐1‐propyne with Triisopropylsilyl Trifluoromethanesulfonate.2Purification: by distillation or chromatography.Handling, Storage, and Precautions: no special precautions required; the reagent is not changed when stored for several months at ambient temperature. The Li derivative is handled under inert gas using simple syringe equipment.
KW - Chemistry
UR - https://www.mendeley.com/catalogue/b400702e-aef3-38f0-a2f5-cbc02d439d42/
U2 - 10.1002/047084289X.rb206
DO - 10.1002/047084289X.rb206
M3 - Articles for encyclopedia
SN - 0-471-93623-5
SP - 583
EP - 585
BT - Encyclopedia of Reagents for Organic Synthesis
A2 - Paquette, Leo A.
A2 - Denmark, S.
PB - John Wiley & Sons Ltd.
CY - Chichester
ER -