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

Božić Tatjana T. (Faculty of Chemistry, Belgrade)
Sladić Dušan M. (Faculty of Chemistry, Belgrade)
Zlatović Mario V. (Faculty of Chemistry, Belgrade)
Novaković Irena (ICTM - Department of Chemistry, Belgrade)
Trifunović Snežana (Faculty of Chemistry, Belgrade)
Gašić Miroslav J. (Faculty of Chemistry, Belgrade)

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.

Keywords: quinone, avarone, conjugate addition, regioselectivity.