Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Stereoselective Cyclopropanation to Homoquinones from Phenacyl Carbenes Obtained through Quinone-Electrogenerated Bases

Stereoselective Cyclopropanation to Homoquinones from Phenacyl Carbenes Obtained through Quinone-Electrogenerated Bases
Kaouthar Hamrouni, Fructuoso Barba, Belen Batanero, Mohamed Lamine Benkhoud
A series of new (E) and (Z)-benzoyl-homoquinones have been prepared in good yield by the parent quinone-electrogenerated base (EGB) in the presence of α-bromoacetophenones or α-bromopropiophenone. The EGB, obtained when electrolysis of p-benzoquinone, or 1,4-naphthoquinone, is carried out at the reduction potential of their first voltammetric peak, conducted to electrogenerated phenacyl carbenes after halide evolution on the first obtained bromo-enolates. The stereoselectivity of the [2 + 2]cycloaddition of the carbene to the quinoid substrate is highly dependent on the electrode nature. Reaction mechanism proposal is discussed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00925

DOI: 10.1021/acs.joc.7b00925

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