Photorelease of HCl from o-Methylphenacyl Chloride Proceeds through the Z-Xylylenol
| Authors | |
|---|---|
| Year of publication | 2001 |
| Type | Article in Periodical |
| Magazine / Source | The Journal of the American Chemical Society |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | photochemistry; photoenolization |
| Description | 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. |
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