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

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 o...

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Bibliographic Details
Main Authors: Božić Tatjana T., Sladić Dušan M., Zlatović Mario V., Novaković Irena, Trifunović Snežana, Gašić Miroslav J.
Format: Article
Language:English
Published: Serbian Chemical Society 2002-01-01
Series:Journal of the Serbian Chemical Society
Subjects:
Online Access:http://www.doiserbia.nb.rs/img/doi/0352-5139/2002/0352-51390209547B.pdf
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Summary: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.
ISSN:0352-5139
1820-7421