1,1',1''-(Chlorosilylidyne)tris(benzene) → Azidotriphenylsilane

HRID 1863200

Reaktionsgleichung

Reaktionsgleichung von HRID 1863200
[C:1]1([Si:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:21]=[N+:22]=[N-:23].[Li+]>O1CCCC1>[C:1]1([Si:7]([N:21]=[N+:22]=[N-:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 88163Lithium azide

Produkt 1

HCID 79708AzidotriphenylsilaneAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the method of Wiberg et al [Wiberg et al, Angew. Chem. Internat'l Ed.Engl., 1, 335 (1962)] in an inert atmosphere enclosure a solution of triphenylsilylchloride (73.9 g, 0.251 mol) in tetrahydrofuran (400 ml) was stirred with lithium azide (15.3 g, 0.312 mol) at room temperature over a period of 115 hr. After filtration, the solvent was removed in vacuo. The resulting white solid was boiled with heptane (350 ml), filtered hot and allowed to crystallize. Triphenylsilyl azide, 65.5 g (86.3% yield), mp 82°-84° C. was obtained. The melting point and infrared spectrum were identical with that of an authentic sample.

Aufarbeitung

  1. filtrationAfter filtration
  2. customthe solvent was removed in vacuo
  3. filtrationfiltered hot
  4. customto crystallize

Quellen und Nachweise

ORD-Eintrag
ord-d8c4c5b25dce4a99a0091fa63cc0786a
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04168287

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