| PLÍŠTIL, Lukáš, Tomáš ŠOLOMEK, Jakob WIRZ, Dominik HEGER a Petr KLÁN. Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2006, roč. 71, č. 21, s. 8050-8058. ISSN 0022-3263. |
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@article{769252,
author = {Plíštil, Lukáš and Šolomek, Tomáš and Wirz, Jakob and Heger, Dominik and Klán, Petr},
article_location = {Columbus, OH, USA},
article_number = {21},
keywords = {Photochemistry; phenacyl group; photoenolization},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate},
volume = {71},
year = {2006}
}
TY - JOUR
ID - 769252
AU - Plíštil, Lukáš - Šolomek, Tomáš - Wirz, Jakob - Heger, Dominik - Klán, Petr
PY - 2006
TI - Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate
JF - Journal of Organic Chemistry
VL - 71
IS - 21
SP - 8050-8058
EP - 8050-8058
PB - the American Chemical Society
SN - 00223263
KW - Photochemistry
KW - phenacyl group
KW - photoenolization
N2 - 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.
ER -
PLÍŠTIL, Lukáš, Tomáš ŠOLOMEK, Jakob WIRZ, Dominik HEGER a Petr KLÁN. Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2006, roč.~71, č.~21, s.~8050-8058. ISSN~0022-3263.
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