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

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Title: Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes
Authors: Byrne, Peter A.
Higham, Lee J.
McGovern, Pádraic
Gilheany, Declan G.
Permanent link: http://hdl.handle.net/10197/4938
Date: Dec-2012
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.
Type of material: Journal Article
Publisher: Elsevier
Copyright (published version): 2012 Elsevier Ltd
Keywords: Wittig reaction mechanism;Keto-stabilised phosphonium ylide;ortho-Substituted benzaldehydes;Kinetic control in Wittig reactions;Z-Alkene;[2+2] Cycloaddition
DOI: 10.1016/j.tetlet.2012.09.123
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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