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Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones

Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone

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2002
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Authors
Božić, Tatjana T.
Sladić, Dušan
Zlatović, Mario
Novaković, Irena
Trifunović, Snežana
Gašić, Miroslav J.
Article (Published version)
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Abstract
The regioselectivity of the reaction of conjugate addition of thiols amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl- 1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones.
Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona.
Keywords:
quinone / avarone / conjugate addition / regioselectivity
Source:
Journal of the Serbian Chemical Society, 2002, 67, 8-9, 547-551
Publisher:
  • Serbian Chemical Society
Funding / projects:
  • Project MESTD, br. 1586

DOI: 10.2298/JSC0209547B

ISSN: 0352-5139

WoS: 000178039500001

Scopus: 2-s2.0-0036378018
[ Google Scholar ]
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/55
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Božić, Tatjana T.
AU  - Sladić, Dušan
AU  - Zlatović, Mario
AU  - Novaković, Irena
AU  - Trifunović, Snežana
AU  - Gašić, Miroslav J.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/55
AB  - The regioselectivity of the reaction of conjugate addition of thiols amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl- 1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones.
AB  - Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones
T1  - Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone
VL  - 67
IS  - 8-9
SP  - 547
EP  - 551
DO  - 10.2298/JSC0209547B
ER  - 
@article{
author = "Božić, Tatjana T. and Sladić, Dušan and Zlatović, Mario and Novaković, Irena and Trifunović, Snežana and Gašić, Miroslav J.",
year = "2002",
abstract = "The regioselectivity of the reaction of conjugate addition of thiols amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl- 1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones., Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones, Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone",
volume = "67",
number = "8-9",
pages = "547-551",
doi = "10.2298/JSC0209547B"
}
Božić, T. T., Sladić, D., Zlatović, M., Novaković, I., Trifunović, S.,& Gašić, M. J.. (2002). Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 67(8-9), 547-551.
https://doi.org/10.2298/JSC0209547B
Božić TT, Sladić D, Zlatović M, Novaković I, Trifunović S, Gašić MJ. Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones. in Journal of the Serbian Chemical Society. 2002;67(8-9):547-551.
doi:10.2298/JSC0209547B .
Božić, Tatjana T., Sladić, Dušan, Zlatović, Mario, Novaković, Irena, Trifunović, Snežana, Gašić, Miroslav J., "Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones" in Journal of the Serbian Chemical Society, 67, no. 8-9 (2002):547-551,
https://doi.org/10.2298/JSC0209547B . .

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