An unusual fragmentation of oxetane-embedded tetracyclic ketal systems

Mangeswara Rao, G H and Khan, Faiz Ahmed (2013) An unusual fragmentation of oxetane-embedded tetracyclic ketal systems. Journal of Organic Chemistry, 78 (21). pp. 11092-11095. ISSN 0022-3263

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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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IITH Creators:
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Item Type: Article
Uncontrolled Keywords: Cyclobutanes; Fragmentation reactions; Functionalized; High yield; Norbornane; Side products
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 15 Nov 2014 09:08
Last Modified: 21 Sep 2017 06:44
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