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

Participants

Reaction Steps

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:

Provenance & Evidence