INTRAMOLECULAR CYCLOADDITIONS OF ARYLKETENES WITH ALKENES. REACTIONS OF 5-ARYLBICYCLOHEPTAN-6-ONES.

Article abstract of DOI:10.1016/0040-4039(88)85114-1

Intramolecular cycloadditions of arylketenes 4 proceed in excellent yield to give 5-arylbicyclo<3.2.0>heptan-6-ones 5.Reaction of 5a with KOH in THF gives a 95:5 mixture of 7 and 10.Reaction of 5a with KOEt in ETOH give a 1:3 mixture of 7 and 10.Reaction of 5a with vinyllithium and treatment of the resulting alcohol 23 with KH gives the 1,3-sigmatropic rearrangement product 25.