Acetone → 2-Methylideneadamantane

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyltriphenylphosphonium bromide (14 g; 39.17 mmol) in 100 ml of ether cooled to 0° C. under argon was added dropwise n-butyllithium (2.51 g; 39.17 mmol) in hexane (15.7 mml). An ice-bath was removed and the mixture was allowed to react at room temperature for 2 hours. After cooling the reaction mixture to 0° C., a suspension of 5.35 g (35.61 mmol) of 2-adamantanone in ether (25 ml) was added and the mixture was stirred at room temperature for 2 hours. Acetone was added to decompose the phosphonium salt, the reaction mixture was filtered and the residue was washed with ether. The combined organic layer was distilled in vacuo and the residue was redissolved in ether and cooled to 0° C. to yield 3.5 g (66.4%) of 2-methylene-adamantane (see J. Org. Chem. 1985, 54, 1375) (Formula III: R2 =R3 =H; R4 and R5 together are adamantanyl), as a low melting solid.

Provenance & Evidence