Oxygen → HCID 54574644, compound

Participants

Reaction Conditions

Reaction Steps

Allylmagnesium bromide (50 mmoles) and bicyclo[2.2.1]hepta-2,5-diene (50 mmoles) were reacted in diethyl ether in a sealed bomb by heating for 2.25 hours at 125° C. and one hour at 140° C. The reaction product was then oxidized at 0° C. by passing gaseous oxygen through the product for about 30 minutes. The resultant product was then hydrolyzed with water followed by aqueous ammonium chloride solution and then water. After drying the product over anhydrous magnesium sulfate, the diethyl ether solvent was removed using a steam bath. The product was vacuum distilled and the fraction boiling at 95°-101° C. at 2.5-3 mm Hg was collected. This product, tricyclo[4.2.1.02,5 ]non-7-en-3-ylmethanol, was isolated in a 70 percent yield and its structure was supported by the results of nuclear magnetic resonance studies. It may be depicted as follows: ##STR1##

Provenance & Evidence