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Intramolecular cycloadditions of arylketenes with alkenes: Reactions of 5-arylbicyclo[3.2.0]heptan-6-ones
Journal article   Peer reviewed

Intramolecular cycloadditions of arylketenes with alkenes: Reactions of 5-arylbicyclo[3.2.0]heptan-6-ones

Barry B Snider and Maho Niwa
Tetrahedron letters, Vol.29(26), pp.3175-3178
1988

Abstract

Alicyclic Compounds Organic Chemistry
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.

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