ELECTROREDUCTIVE CYCLIZATION REACTIONS: ATTEMPTS TO USE 2(5H)FURANONES (α,β-UNSATURATED BUTENOLIDES). DOMINANCE OF ACID-BASE OVER CYCLIZATION CHEMISTRY

Article abstract of DOI:10.1016/S0040-4020(01)90497-1

The potential utility of butenolides as substrates in the electroreductive cyclization reaction has been investigated.A variety of butenolides bearing either an α,β,γ,δ-unsaturated ester, allylic bromide, bromide, mesylate or aldehyde functionality on the appending side chain have been examined.The performance of each of these systems under electroreductive cylization reaction conditions is severely limited by the presence of acidic protons at C5 of the butenolide ring and at C1 of the appending side chain.