Hammett analysis of photodecarbonylation of crystalline 1,3-diphenylacetones

ORGN 465

Marino J. E. Resendiz, resendiz@chem.ucla.edu and Miguel A. Garcia-Garibay, mgg@chem.ucla.edu. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA 90095
It has been suggested that reactions in crystals can be engineered from known molecular structure parameters. Herein, the effect of aromatic substituents on the á-cleavage and decarbonylation steps in the solid state decarbonylation reaction of 1,3-diarylacetones was studied. The relative quantum yields and chemical efficiencies of crystalline p,p'-disubstituted 1,3-diphenyl-2-propanones with MeO-, Me-, F-, CF3-, and 3,4-diMeO- groups were determined by parallel irradiation of polycrystalline samples. The results suggest the effect of substituents to be modest, but not much more complex than analogous results in solution. This leads the way towards the elucidation of common patterns suitable for the prediction of chemical reactivity and selectivity in solid-state reactions.
 

New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005