1,3-Bis(triisopropylsilyl)propyne

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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.
Original languageEnglish
Title of host publicationEncyclopedia of Reagents for Organic Synthesis : Band 1
EditorsLeo A. Paquette, S. Denmark
Number of pages3
Place of PublicationChichester
PublisherJohn Wiley & Sons Ltd.
Publication date1995
Pages583-585
ISBN (print)0-471-93623-5
DOIs
Publication statusPublished - 1995
Externally publishedYes

DOI