HCID 22753443, compound → Propanedinitrile, [bis[3,5-bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene]cyclopropylidene]-

HRID 2163325Notes

Reaction equation

HRID 2163325 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:18](=[C:19]([C:22]#[N:23])[C:20]#[N:21])[C:17]=2[C:24]2[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([OH:34])=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:25]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>[OH-].[K+].C(Cl)(Cl)Cl.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:35]([C:26]1[C:27](=[O:34])[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:29][C:24](=[C:17]2[C:18](=[C:19]([C:22]#[N:23])[C:20]#[N:21])[C:16]2=[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10](=[O:11])[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8]2)[CH:25]=1)([CH3:36])([CH3:37])[CH3:38]

Participants

5

Reactant 1

HCID 22753443HCID 22753443, compound

Product 1

HCID 113105Propanedinitrile, [bis[3,5-bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene]cyclopropylidene]-Yield 98.3%

Reagents, catalysts & solvents 3

HCID 178511488HCID 178511488, compoundCatalystHCID 6212ChloroformSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1.00 g (3.04 mmol) of potassium ferricyanide in 20 ml of 1N KOH solution was added to a solution of 0.51 g (1.0 mmol) of 6a in 20 ml of chloroform. The deep blue two-phase mixture was stirred vigorously at room temperature for 1 hr under a nitrogen atmosphere. The organic layer was separated, washed with water, dried (MgSO4) and evaporated in vacuo to give 0.50 g (98%) of 5a as golden plates after recrystallization from hexane; mp 210-215° (dec); ir (KBr) 2960-2860(m), 2227(w), 2217(w), 1753(m), 1600(s), 1525(w), 1510(w), 1470(s), 1360(m), 1345(m), 1260(w), 1115(s), 1020(w), 950(w), 910(m), 830 cm-1 (w); nmr (CDCl3) δ 1.34(s, 18H), 1.38(s, 18H0); 7.45(d,J = 2Hz, 2H), 7.71 (d, J = 2Hz, 2H); uv-visible, λmax (benzene) 319(sh) (3.77), 345(sh) (3.90), 364(4.03), 387(sh) (4.01), 415(sh) (3.88), 498 (sh) (3.96), 548(sh) (4.40), 587(4.79), 609 (4.80), 640(sh) (4.25); mass spectrumm/e 508.31003 (calcd 508.30897); Anal. Calcd for C34H40N2O2 : C, 80.27; H, 7.93; N, 5.51. Found: C, 80.40; H, 8.09; N, 5.48.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a7cdae68a86a45de92da8cb99be09c2a
Source dataset
uspto-grants-1979_01
Patent number
US04133821

Reaction notes

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