Toluene → 1,2,3,4,6,7,8,8a-Octahydro-1,6-methanonaphthalene

HRID 259511Notes

Reaction equation

HRID 259511 reaction equation
[NH2-].[Na+].[C:3]1([CH3:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>>[CH:3]12[CH2:9][CH:5]3[CH:6]([CH2:7][CH2:8]1)[C:5]([CH2:8][CH2:3][CH2:4]3)=[CH:4]2

Participants

3

Reactant 2

HCID 1140Toluene2×HCID 24533Sodium amide

Product 1

HCID 539812491,2,3,4,6,7,8,8a-Octahydro-1,6-methanonaphthaleneYield 52%

Procedure

To a solution of 8.22 g (36 millimoles) of 3-bromo-4-homoisotwistane in 20 ml of dry toluene was added 1.4 g (36 millimoles) of sodium amide, and the mixture was stirred for 2 hours under reflux of toluene. After completion of the reaction, the reaction mixture was filtered and the filtrate was fractionally distilled to give 2.75 g (52% yield) of colorless tricyclo[5.3.1.03,8 ]undec-2-ene (boiling point of 90° to 92° C/19 mm Hg). Elementary Analysis Values:

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. distillationthe filtrate was fractionally distilled

Sources & evidence

ORD record
ord-34d461afdd694d5884234c6e410107ae
Source dataset
uspto-grants-1977_07
Patent number
US04038333

Reaction notes

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