Expression of concern: A unifying mechanism for the rearrangement of vinyl allene oxide geometric isomers to cyclopentenones

Abstract

Expression of concern for ‘A unifying mechanism for the rearrangement of vinyl allene oxide geometric isomers to cyclopentenones’ by Adán B. González-Pérez et al., Org. Biomol. Chem., 2014, 12, 7694–7701.

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The following article ‘A unifying mechanism for the rearrangement of vinyl allene oxide geometric isomers to cyclopentenones’ by Adán B. González-Pérez, Alexander Grechkin and Ángel R. de Lera has been published in Organic & Biomolecular Chemistry. The article reports that Z-Vinyl allene oxides are predicted to rearrange with high fidelity to stereodefined cyclopentenones through intermediate cyclopropanones.

The Royal Society of Chemistry has been contacted by the corresponding author of this article to inform us that they have found an error in the calculations in the article. The authors overlooked in their calculations the existence of diradical triplet states in some of the structures. They inform us that taking them into account could change the main findings of the mechanistic proposal based on the formation and rearrangement of cyclopropanones, which were left as the only explanation of the experimentally observed enantioselective for the rearrangement of Z vinyl allene oxides, but not of the E isomers.

Organic & Biomolecular Chemistry is publishing this expression of concern in order to alert our readers of these concerns. The authors are currently carrying out a further study in order to assess the impact that this has on the findings in the manuscript. An expression of concern will continue to be associated with this manuscript until the authors inform us of the outcome of this further study, and we will work with the authors to ensure readers are notified of any implications this has for the results published in this article.

Richard Kelly

4th November 2015

Executive Editor, Organic & Biomolecular Chemistry

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