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

HRID 372860

Reaction equation

HRID 372860 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 79708AzidotriphenylsilaneYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 crystalline. 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.

Workup

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

Sources & evidence

ORD record
ord-d5d14d4567ef47a8b8a66339a87e0291
Source dataset
uspto-grants-1978_05
Patent number
US04092466

Linked notes

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