Mechanism
In the first step of the mechanism, the alcohol (1) coordinates to the aluminum to form a complex (3), which then, in the second step, gets deprotonated by an alkoxide ion (4) to generate an alkoxide intermediate (5). In the third step, both the oxidant acetone (7) and the substrate alcohol are bound to the aluminum. The acetone is coordinated to the aluminum which activates it for the hydride transfer from the alkoxide. The aluminium-catalyzed hydride shift from the α-carbon of the alcohol to the carbonyl carbon of acetone proceeds over a six-membered transition state (8). The desired ketone (9) is formed after the hydride transfer.
Read more about this topic: Oppenauer Oxidation
Famous quotes containing the word mechanism:
“The law isn’t justice. It’s a very imperfect mechanism. If you press exactly the right buttons and are also lucky, justice may show up in the answer. A mechanism is all the law was ever intended to be.”
—Raymond Chandler (1888–1959)
“I’ve never known a Philadelphian who wasn’t a downright “character;” possibly a defense mechanism resulting from the dullness of their native habitat.”
—Anita Loos (1888–1981)
“Life is an offensive, directed against the repetitious mechanism of the Universe.”
—Alfred North Whitehead (1861–1947)