Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes

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dc.contributor.author Byrne, Peter A.
dc.contributor.author Higham, Lee J.
dc.contributor.author McGovern, Pádraic
dc.contributor.author Gilheany, Declan G.
dc.date.accessioned 2019-04-04T14:09:11Z
dc.date.available 2019-04-04T14:09:11Z
dc.date.issued 2012-10-02
dc.identifier.citation Byrne, P. A., Higham, L. J., McGovern, P. and Gilheany, D. G. (2012) 'Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes', Tetrahedron Letters, 53(49), pp. 6701-6704. doi: 10.1016/j.tetlet.2012.09.123 en
dc.identifier.volume 53 en
dc.identifier.startpage 6701 en
dc.identifier.endpage 6704 en
dc.identifier.issn 0040-4039
dc.identifier.uri http://hdl.handle.net/10468/7716
dc.identifier.doi 10.1016/j.tetlet.2012.09.123 en
dc.description.abstract Wittig reaction products of keto-stabilised ylides with ortho-substituted benzaldehydes are found to show significantly higher than expected Z-alkene content (up to 50%) compared to analogous reactions of the same ylides with benzaldehyde itself. A cooperative effect is seen whereby the unusual Z-content is further augmented if the ylide bears greater steric bulk in the α′-position. These results are consistent with our previous observations on reactions of all ylide types with aldehydes bearing a β-heteroatom. Significantly, the cooperative effect, previously seen only with semi-stabilised ylides, has now been extended to stabilised ylides. Both the anomalous increase in Z-content and the cooperative effect can be rationalised within the [2+2] cycloaddition mechanism of the Wittig reaction. en
dc.description.sponsorship Irish Research Council for Science, Engineering and Technology (EMBARK Scholarship) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Elsevier en
dc.relation.uri http://www.sciencedirect.com/science/article/pii/S0040403912017236
dc.rights © 2012 Elsevier Ltd. All rights reserved. This submitted manuscript version is made available under the CC-BY-NC-ND 4.0 license en
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/4.0/ en
dc.subject Wittig reaction mechanism en
dc.subject Keto-stabilised phosphonium ylide en
dc.subject ortho-Substituted benzaldehydes en
dc.subject Kinetic control in Wittig reactions en
dc.subject Z-Alkene en
dc.subject [2+2] Cycloaddition en
dc.title Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Peter Byrne, Chemistry, University College Cork, Cork, Ireland. +353-21-490-3000 Email: peter.byrne@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2019-03-26T18:26:06Z
dc.description.version Submitted Version en
dc.internal.rssid 383418264
dc.contributor.funder Irish Research Council for Science, Engineering and Technology en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Tetrahedron Letters en
dc.internal.copyrightchecked No
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress peter.byrne@ucc.ie en


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© 2012 Elsevier Ltd. All rights reserved. This submitted manuscript version is made available under the CC-BY-NC-ND 4.0 license Except where otherwise noted, this item's license is described as © 2012 Elsevier Ltd. All rights reserved. This submitted manuscript version is made available under the CC-BY-NC-ND 4.0 license
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