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:
“A mechanism of some kind stands between us and almost every act of our lives.”
—Sarah Patton Boyle, U.S. civil rights activist and author. The Desegregated Heart, part 3, ch. 2 (1962)
“When one of us dies of cancer, loses her mind, or commits suicide, we must not blame her for her inability to survive an ongoing political mechanism bent on the destruction of that human being. Sanity remains defined simply by the ability to cope with insane conditions.”
—Ana Castillo (b. 1953)
“Life is an offensive, directed against the repetitious mechanism of the Universe.”
—Alfred North Whitehead (1861–1947)