OXIDATIVE CLEAVAGE OF AN ALKENE WITH CATALYTIC RUTHENIUM TETROXIDE

Oxidative cleavage of an alkene with catalytic ruthenium tetroxide; 2-acylphenylacetic acid

SyntheticPage 186 (2002)

Submitted 11th Mar 2002, published 12th Mar 2002

Meriel Kimberley (meriel.kimberley@https://www.360docs.net/doc/f410199713.html,),

A contribution from the Booker-Milburn Group, Bristol

Chemicals Used

3-methyl-indene, sodium periodate (Aldrich), ruthenium trichloride hydrate (Aldrich), acetonitrile (HPLC grade, Aldrich), hexane water Procedure

To a solution of 3-methyl-indene (497 mg, 3.8 mmol) in acetonitrile (7 ml), hexane (7 ml) and water (10 ml) was added sodium periodate (3.35 g, 15.7 mmol) followed by ruthenium trichloride (17 mg, 0.08 mmol, 2.2 mol%). The entire mixture was then stirred at room temperature for 2 hours until the reaction was complete (TLC). Dichloromethane was then added (30 ml), the phases separated and the upper phase was extracted with dichloromethane (3 x 30 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Diethyl ether was added to the resulting residue (to precipitate any remaining inorganic species). The resulting solution was filtered through a pad of celite and concentrated to afford the crude keto-acid which could be used without further purification. Pure compound can be obtained by recrystallisation from ethyl acetate.

Author's Comments

Care should be taken to ensure vigorous stirring after addition of ruthenium trichloride as the reaction solution can get very warm. Data

1H (CDCl3): 7.84 (1H, d, J 7.7 Hz, CH), 7.51 (1H, t, J 7.7 Hz, CH), 7.42 (1H, t, J 8 Hz), 7.35 (1H, d, J 8 Hz, CH), 3.91 (2H, s, CH2) and 2.65 (3H, s, CH3).

Lead Reference

P. H. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, https://www.360docs.net/doc/f410199713.html,. Chem., 1981, 46, 19, 3936-3938.

Other References

M. Shindo, Y. Sato, K. Shishido, J. Org. Chem., 2001, 66, 23, 7818-7824.