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Correction and removal of expression of concern: A unifying mechanism for the rearrangement of vinyl allene oxide geometric isomers to cyclopentenones

Richard Kelly
Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge, CB4 0WF, UK. E-mail: obc-rsc@rsc.org

Received 6th March 2017 , Accepted 6th March 2017

First published on 17th March 2017


Correction and removal of 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.


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.

Organic & Biomolecular Chemistry published an expression of concern (Org. Biomol. Chem., 2015, 13, 11580) in order to alert our readers to concerns expressed to us by the authors following publication due to 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 informed 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 enantioselectivity for the rearrangement of Z vinyl allene oxides, but not of the E isomers.

The authors have now published a new article which addresses their concerns about the error in their original calculations. The new article is:

‘Rearrangement of vinyl allene oxide geometric isomers to cyclopentenones. Further computational insights with biologically relevant model systems’ by Adán B. González-Pérez et al., Org. Biomol. Chem., 2017, DOI: 10.1039/c6ob02791a

Accordingly, Organic & Biomolecular Chemistry is officially removing its expression of concern.

Richard Kelly

6th March 2017

Executive Editor, Organic & Biomolecular Chemistry


This journal is © The Royal Society of Chemistry 2017