| KLÁN, Petr, Radovan RŮŽIČKA, Dominik HEGER, Jaromír LITERÁK, Petr KULHÁNEK and André LOUPY. Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole. Photochemical and Photobiological Sciences. Cambridge, United Kingdom: Royal Society of Chemistry, 2002, vol. 1, No 12, p. 1012-1017. ISSN 1474-905X. |
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@article{406620,
author = {Klán, Petr and Růžička, Radovan and Heger, Dominik and Literák, Jaromír and Kulhánek, Petr and Loupy, André},
article_location = {Cambridge, United Kingdom},
article_number = {12},
keywords = {microwave; photochemistry},
language = {eng},
issn = {1474-905X},
journal = {Photochemical and Photobiological Sciences},
title = {Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole},
volume = {1},
year = {2002}
}
TY - JOUR
ID - 406620
AU - Klán, Petr - Růžička, Radovan - Heger, Dominik - Literák, Jaromír - Kulhánek, Petr - Loupy, André
PY - 2002
TI - Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole
JF - Photochemical and Photobiological Sciences
VL - 1
IS - 12
SP - 1012
EP - 1012
PB - Royal Society of Chemistry
SN - 1474905X
KW - microwave
KW - photochemistry
N2 - A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by the hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature in the region of -20 to 196 oC. The quantum yield of the 4-methoxyphenol formation was found to be temperature independent, in contrast to that of the 4-nitrophenol formation, suggesting that there is a temperature dependent process occurring after the partitioning between replacement of the nitro group and the methoxy group has taken place. The reaction was also investigated by the quantum chemical calculations. A technique for microwave-assisted photochemical synthesis is proposed as an efficient and practical tool for organic synthesis
ER -
KLÁN, Petr, Radovan RŮŽIČKA, Dominik HEGER, Jaromír LITERÁK, Petr KULHÁNEK and André LOUPY. Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole. \textit{Photochemical and Photobiological Sciences}. Cambridge, United Kingdom: Royal Society of Chemistry, 2002, vol.~1, No~12, p.~1012-1017. ISSN~1474-905X.
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