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 T.
Trifunović, Snežana S.
Gasic, MJ
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 / avarone / conjugate addition / conjugate addition / regioselectivity / regioselectivitySource:
Journal of the Serbian Chemical Society, 2002, 67, 8-9, 547-551Publisher:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0209547B
ISSN: 0352-5139
WoS: 000178039500001
Scopus: 2-s2.0-0036378018
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Božić, Tatjana T. AU - Sladić, Dušan AU - Zlatović, Mario AU - Novaković, Irena T. AU - Trifunović, Snežana S. AU - Gasic, MJ PY - 2002 UR - https://cherry.chem.bg.ac.rs/handle/123456789/506 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 Soc, Belgrade 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 T. and Trifunović, Snežana S. and Gasic, MJ", 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 Soc, Belgrade", 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. T., Trifunović, S. S.,& Gasic, M.. (2002). Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 67(8-9), 547-551. https://doi.org/10.2298/JSC0209547B
Božić TT, Sladić D, Zlatović M, Novaković IT, Trifunović SS, Gasic M. 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 T., Trifunović, Snežana S., Gasic, MJ, "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 . .