Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate

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Publikace nespadá pod Ekonomicko-správní fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
Název česky Fotochemie 2-alkoxynethyl-5-methylfenacyl chloridu a benzoatu
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PLÍŠTIL Lukáš ŠOLOMEK Tomáš WIRZ Jakob HEGER Dominik KLÁN Petr

Rok publikování 2006
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of Organic Chemistry
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
Obor Organická chemie
Klíčová slova Photochemistry; phenacyl group; photoenolization
Popis Irradiation of 2-(alkoxymethyl)-5-methyl--chloroacetophenones (1a-c) and 2-(methoxymethyl)-5-methylphenacyl benzoate (1d) in dry, nonnucleophilic solvents afforded 3-alkoxy-6-methylindan-1-ones (3a-c) in very high chemical yields. 3-Methylisobenzofuran-1(3H)-one (2) was, however, isolated as a major photoproduct in the presence of trace amounts of water. Quenching experiments and laser flash spectroscopy revealed that the indanone derivatives 3 are formed by 1,5-hydrogen migration from the lowest triplet excited state of the acetophenones 1 and cyclization of the resulting photoenols. In contrast, production of the lactone 2 in wet solvents was found to result from two consecutive photochemical transformations. The photoenols produced by photolysis of 1a-c add water as a nucleophile to form 2-acetyl-4-methylbenzaldehyde (4), which is further converted to 2 via a second, singlet state photoenolization process. Exhaustive photolysis of 1a in methanol produced the acetal 2-(dimethoxymethyl)-5-methylacetophenone (7a) as the exclusive product. The remarkable selectivity of these photoreactions may well be useful in synthetic organic chemistry.
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