ORGN 448 |
| p-Hydroxyphenacyl (pHP) protected substrates release substrates through a novel photo-Favorskii rearrangement, Scheme 1. In an effort to systematically explore the effects of the leaving group on the efficacy of the photorelease, a series of pHP substituted benzoate and sulfonate esters have been examined. The quantum yields, Stern-Volmer quenching rates, and release rates were determined along with pH rate profiles for all of the leaving groups. The results suggest that the leaving group nucleofugacity does influence the rate and efficiency of the photorelease process. Quantitative evaluations of the structure-photoreactivity relationships have been explored. These results and the mechanistic details will be presented.
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Physical Organic Chemistry: Calculations, Mechanisms, Photochemistry, and High Energy Species
1:00 PM-4:40 PM, Tuesday, August 21, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
