Solvent dependence in the rhodium-catalyzed cyclization of o-vinyl benzaldehyde

ORGN 572

Darryl V. French, DVF0406@MAIL.ECU.EDU and Andrew T. Morehead Jr., moreheada@mail.ecu.edu. Department of Chemistry, East Carolina University, Science and Technology Building, Greenville, NC 27858
Rhodium-catalyzed intramolecular hydroacylation of ortho-vinyl benzaldehyde (1) results in a dimer (3) being formed in an approximate ratio of 2:1 with the anticipated indanone (2). This reaction shows an unusual reaction course as it accelerates when the concentration of vinyl benzaldehyde is reduced, and in addition the dimer and indanone are formed in the same ratio irrespective of starting material concentration. Kinetic studies in different solvents and in the presence of indanone were carried out to examine how the rate and product ratio are influenced by choice of conditions.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006