Hammett analysis of photodecarbonylation in crystalline 1,3-diarylacetones

Marino J E Resendiz; Miguel A Garcia-Garibay

doi:10.1021/ol0480527

Hammett analysis of photodecarbonylation in crystalline 1,3-diarylacetones

Org Lett. 2005 Feb 3;7(3):371-4. doi: 10.1021/ol0480527.

Authors

Marino J E Resendiz¹, Miguel A Garcia-Garibay

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, USA.

PMID: 15673242
DOI: 10.1021/ol0480527

Abstract

[reaction: see text] The relative quantum yields and chemical efficiencies of crystalline p,p'-disubstituted 1,3-diphenyl-2-propanones with 4-MeO, 4-Me, 4-F, 4-CF3, and 3,4-diMeO groups were determined by parallel irradiation of polycrystalline samples. Variations in quantum yields that span a factor of 4 are analyzed in terms of the effects of substituents on the stability of the benzylic radical. All solid-state reactions proceeded with 100% chemoselectivity and in >95% chemical yield.