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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An unusual fragmentation of oxetane-embedded tetracyclic ketal systems
G Hari Mangeswara Rao1, Faiz Ahmed Khan
1Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur-208016, India.
Abstract:
An unusual route for the synthesis of functionalized cyclobutane derivatives starting from functionalized norbornane derivatives is reported. Base-induced fragmentation of an oxetanol-type moiety embedded in a tetracyclic norbornyl ketal leads to a cyclobutane-fused derivative as the major or exclusive product. The fragmentation reaction for bridgehead-bromine-substituted derivatives was much faster than for the corresponding chlorine-substituted substrates. The functionalized cyclobutane product was formed exclusively in high yield in the former case, while the latter furnished a minor uncyclized side product in varying yields.
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