Tetrahedron letters

Intramolecular cycloadditions of arylketenes with alkenes: Reactions of 5-arylbicyclo [3.2. 0] heptan-6-ones

BB Snider, M Niwa

Index: Snider, Barry B.; Niwa, Maho Tetrahedron Letters, 1988 , vol. 29, # 26 p. 3175 - 3178

Full Text: HTML

Citation Number: 10

Abstract

Abstract Intramolecular cycloadditions of arylketenes 4 proceed in excellent yield to give 5- arylbicy-clo [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.