Volume 27, Issue 23
Isocyclic Compounds
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ChemInform Abstract: Double Ring Expansions: A New Method for Making Medium and Large Cyclic Ketones.

W. ZHANG

W. ZHANG

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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P. DOWD

P. DOWD

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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First published: June 4, 1996

Abstract

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ChemInform Abstract

Large cyclic ketones such as (V), (VI), and (VII) are prepared by a free radical ring expansion of the cyclobutenones (I) followed by fluoride-induced Grob fragmentation of (IV). The cyclobutenones, e.g. ( Ic), are easily obtained by a (2 + 2) cycloaddition of bromoalkylketenes to cyclic enol ethers such as (VIII).

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