Sodium bis(trimethylsilyl)amide → Isophthalonitrile

HRID 655047Notes

Reaction equation

HRID 655047 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]#[N:30])[CH:28]=1)C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:2].[Br-].C(C1C=C(C=C(C#N)C=1)C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#N.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[C:29](#[N:30])[C:27]1[CH:26]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:28]=1

Participants

4

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 19887125HCID 19887125, compoundHCID 19887147HCID 19887147, compound

Product 1

HCID 12276Isophthalonitrile

Procedure

kk) by using 3,5-dicyanobenzylidenetriphenylphosphorane prepared in situ by means of 3,5-dicyanobenzyltriphenylphosphonium bromide and sodium bis(trimethylsilyl)amide there is obtained 5-[(Z)-2-(1R,4S,5S,8R)-4,8-dimethyl-7-oxo-2,3-dioxabicyclo[3.3.1]nonan-4-yl]vinyl]isophthalonitrile [m.p. 85°];

Sources & evidence

ORD record
ord-4af9701447b547ff96e654b9faa4c337
Source dataset
uspto-grants-1992_07
Patent number
US05134240

Reaction notes

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