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Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes
Date Issued
2012-12
Date Available
2013-11-19T09:47:33Z
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
Journal
Tetrahedron Letters
Volume
53
Issue
49
Start Page
6701
End Page
6704
Copyright (Published Version)
2012 Elsevier Ltd
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
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