| Originalsprache | Englisch |
|---|---|
| Titel | Encyclopedia of Reagents for Organic Synthesis : Band 1 |
| Herausgeber | Leo A. Paquette, S. Denmark |
| Anzahl der Seiten | 3 |
| Erscheinungsort | Chichester |
| Verlag | John Wiley & Sons Ltd. |
| Erscheinungsdatum | 1995 |
| Seiten | 583-585 |
| ISBN (Print) | 0-471-93623-5 |
| DOIs | |
| Publikationsstatus | Erschienen - 1995 |
| Extern publiziert | Ja |
1,3-Bis(triisopropylsilyl)propyne
Publikation: Beiträge in Sammelwerken › Lexikonbeiträge › Forschung
Authors
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,14H2,1‐12H3
InChIKey = 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.2
Purification: 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.
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,14H2,1‐12H3
InChIKey = 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.2
Purification: 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.
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