A. P. Pelliccioli, P. Klán, M. Zabadal
Aug 15, 2001
Citations
0
Influential Citations
39
Citations
Journal
Journal of the American Chemical Society
Abstract
Photorelease of HCl from 2,5-dimethylphenacyl chloride (1) was studied by nanosecond laser flash photolysis. 6-Methyl-1-indanone (3) and 2-(methoxymethyl)-5-methylacetophenone (4) are formed by heterolytic elimination of chloride ion from the Z-xylylenol, which is the only photoenol formed in this solvent. The E-isomer is not formed in methanol, because photoenolization from the singlet state is highly efficient, and the triplet pathway does not compete measurably. In benzene solution both the E- and Z-photoenols are formed, but only the E isomer gives product 3 by HCl elimination whereas the Z-isomer decays predominantly by intramolecular reketonization to 1 in this solvent.