Abstract
3-Chloro-3-cyclobutene-1,2-dione (1c) reacts with the dienes 3a-e on careful heating to 110 o C to afford the bicyclo[4.2.0]octa-1(6), 3-diene-7,8-dione 4a-e. The reaction pathway is explained by Diels Alder adduct formation and subsequent elimination of hydrogen chloride. 4a-e are readily oxidized by activated manganese(IV) oxide to give the benzocyclobutenediones 5a-e in good yields. The parent benzocyclobutenedione (5a) has been prepared even more conveniently in a one-pot Diels-Alder route by heating a mixture of 3-chloro-3-cyclobutene-1,2-dione (1c) and 1-acetoxy-1,3-butadiene (3f)
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