Chemistry of bis-spiroacetals. Synthesis of the 1,6,8-trioxadispiro[4.1.5.3]-pentadecane ring system

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dc.contributor.author Baker, R en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2011-09-19T01:48:28Z en
dc.date.issued 1988 en
dc.identifier.citation J CHEM SOC PERK T 1 125-131 Jan 1988 en
dc.identifier.issn 0300-922X en
dc.identifier.uri http://hdl.handle.net/2292/8069 en
dc.description.abstract The syntheses of the unsaturated keto epoxide (4) and saturated keto epoxide (18) are described. In both cases, the key step was the nucleophilic addition of the acetylene (10) to δ-valerolactone. Cyclisation of the keto epoxide (18) in the presence of a catalytic amount of camphorsulphonic acid in dichloromethane led to isolation of a single saturated bis-spiroacetal (21). This selectivity can be explained by the preference of spiroacetals to adopt the conformation in which the ring oxygens are axial to the adjacent ring thus gaining stability from the anomeric effect. Analogous protic or Lewis acid-catalysed intramolecular cyclisation of the unsaturated keto epoxide (4) was not successful under a variety of reaction conditions. The unsaturated bis-spiroacetal (24), however, was prepared by an alternative strategy involving an acid-catalysed cyclisation of (22) to form the unsaturated spiroacetal (23) followed by subsequent conversion into a bis-spiroacetal utilising an oxy-radical generated by photolysis. Formation of the unsaturated bis-spiroacetal (24) from (23) was achieved via a Barton-type reaction involving irradiation of a solution of the spiroacetal (23), iodobenzene diacetate, and iodine in cyclohexane at room temperature. en
dc.language EN en
dc.publisher ROYAL SOC CHEMISTRY en
dc.relation.ispartofseries Journal of the Chemical Society, Perkin Transactions 1 en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Chemistry of bis-spiroacetals. Synthesis of the 1,6,8-trioxadispiro[4.1.5.3]-pentadecane ring system en
dc.type Journal Article en
dc.identifier.doi 10.1039/P19880000125 en
pubs.issue 1 en
pubs.begin-page 125 en
dc.rights.holder Copyright: 1988 Royal Society of Chemistry en
pubs.end-page 131 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 141876 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2011-10-06 en


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