Vinyl Acetate → 5-Vinyloxy-1,3-adamantanediol

Participants

Reaction Conditions

Reaction Steps

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,3,5-adamantanetriol (1 mmol) and vinyl acetate (9 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixture was analyzed by gas chromatography to find that 1,3,5-tris(vinyloxy)adamantane, 3,5-bis(vinyloxy)-1-adamantanol, and 5-vinyloxy-1,3-adamantanediol were produced in yields of 52%, 18%, and 8%, respectively, with a conversion from 1,3,5-adamantanetriol of 97%.

Provenance & Evidence