Temperature-sensitive photochemical aromatic substitution on
4-nitroanisole

J 2002

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

KLÁN, Petr, Radovan RŮŽIČKA, Dominik HEGER, Jaromír LITERÁK, Petr KULHÁNEK et. al.

Basic information

Original name

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

Authors

KLÁN, Petr (203 Czech Republic, guarantor), Radovan RŮŽIČKA (203 Czech Republic), Dominik HEGER (203 Czech Republic), Jaromír LITERÁK (203 Czech Republic), Petr KULHÁNEK (203 Czech Republic) and André LOUPY (250 France)

Edition

Photochemical and Photobiological Sciences, Cambridge, United Kingdom, Royal Society of Chemistry, 2002, 1474-905X

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

RIV identification code

RIV/00216224:14310/02:00006717

Organization unit

Faculty of Science

UT WoS

000180225800013

Keywords in English

microwave; photochemistry

Abstract

V originále

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

Links

GA203/02/0879, research and development project

Name: Vliv mikrovlnného záření na fotochemické reakce

Investor: Czech Science Foundation, Microwave Irradiation Effect on Photochemical Reactions

MSM 143100011, plan (intention)

Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles

Citovat

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.

@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.

Detailed Information on Publication Record