Ketonization of incarcerated acetophenone enol.
A free-standing simple enol has been generated inside a carceplex. Rates of ketonization under various conditions were determined; ketonization is extremely slow as compared to the rate in solution. Complexed water is required, and the mechanism proceeds via formation of an enolate followed by protonation at carbon by the same molecule of water that removed the proton from the enol. Acid or base retards ketonization by removing water from the cavity.
Makeiff
Darren A
DA
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC Canada V6T 1Z1.
Vishnumurthy
Kodumuru
K
Sherman
John C
JC
D000098:Acetophenones / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010782:Photolysis
D000098:Acetophenones; D005030:Ethylenes