Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones
Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone

2002
Authors
Božić, Tatjana T.
Sladić, Dušan

Zlatović, Mario

Novaković, Irena

Trifunović, Snežana

Gašić, Miroslav J.
Article (Published version)
Metadata
Show full item recordAbstract
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 / regioselectivitySource:
Journal of the Serbian Chemical Society, 2002, 67, 8-9, 547-551Publisher:
- Serbian Chemical Society
Funding / projects:
- Project MESTD, br. 1586
DOI: 10.2298/JSC0209547B
ISSN: 0352-5139
WoS: 000178039500001
Scopus: 2-s2.0-0036378018
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IHTMTY - 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 . .