Acetic Acid → Spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropane]-2,3-dione

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Reaction Steps

A solution of spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropan]-2-one (rac), 8.6 g (synthesis: N. J. Turro, JACS, 1980, 102, 6056) in acetic acid, 38 ml, was treated at RT with SeO2 (16.15 g) and the suspension was then heated at reflux for 12 h. The reaction mixture was cooled to RT, filtered and the filter cake was washed with ethyl acetate. The filtrate was made basic with 3N aqueous NaOH and more AcOEt was added. The layers were separated, the organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt: 100% to 90%) to give spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropane]-2,3-dione, (2.5 g) as a yellow solid. MS (ESI): 168 (M+NH4)+.

Provenance & Evidence