| Original language | English |
|---|---|
| Title of host publication | Encyclopedia of Reagents for Organic Synthesis : Band 1 |
| Editors | Leo A. Paquette, S. Denmark |
| Number of pages | 3 |
| Place of Publication | Chichester |
| Publisher | John Wiley & Sons Ltd. |
| Publication date | 1995 |
| Pages | 583-585 |
| ISBN (print) | 0-471-93623-5 |
| DOIs | |
| Publication status | Published - 1995 |
| Externally published | Yes |
1,3-Bis(triisopropylsilyl)propyne
Research output: Contributions to collected editions/works › Articles for encyclopedia › Research
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.
- Chemistry