Volume 31, Issue 12
Isocyclic Compounds
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ChemInform Abstract: Regio- and Stereoselective Oxidative Difunctionalization of Alkylidene Cyclohexenes.

Sang-Phyo Hong

Sang-Phyo Hong

Dep. Chem. Biochem., Univ. Ark., Fayetteville, AR 72701, USA

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Matthias C. McIntosh

Matthias C. McIntosh

Dep. Chem. Biochem., Univ. Ark., Fayetteville, AR 72701, USA

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Tosha Barclay

Tosha Barclay

Dep. Chem. Biochem., Univ. Ark., Fayetteville, AR 72701, USA

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Wally Cordes

Wally Cordes

Dep. Chem. Biochem., Univ. Ark., Fayetteville, AR 72701, USA

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Oxidation of the alkylidene cyclohexene (I) with bromine affords a spirocyclic δ-lactone whereas treatment with I-Cl leads to the γ-lactones (III) and (IV). Interestingly, epoxidation of the related hydroxamic acid (V) results in formation of the δ-lactone oxime (VI).

chemical structure image

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