Solvent effects in the rhodium-catalyzed cyclization of ortho-vinyl benzaldehyde

ORGN 157

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 2-vinyl benzaldehyde (1) results in a dimer (3) being formed in an approximate ratio of 3:1 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.

 

Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007