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Computational study of homogenous gold-catalyzed oxime–oxime rearrangement: Balci–Güven rearrangement

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Abstract

Treatment of N-propargylated pyrrole aldoxime derivatives with gold-based catalyst unexpectedly resulted in oxime–oxime rearrangement, which led to ketoximes. This type of reorganization has not been previously observed in the literature and represents a new rearrangement called the Balci–Güven rearrangement. Based on the experimental findings, the proposed mechanistic pathway was studied. Density functional theory calculations employing wb97xd, m062x, and m06 hybrid functional methods were used to locate and discuss the energetics of the intermediates and the transition states of this rearrangement.

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Acknowledgments

I thank Professor Viktorya Aviyente (Boğaziçi University) for her help with Gaussian. Thanks are also due to the Scientific and Technological Research Council of Turkey (TUBITAK) for the use of its ULAKBIM/TRUBA high performance and grid computing center.

Funding

Financial support from the Scientific Research Department (BAP, Project No. FEF.19001.18.004) of Hitit University is gratefully acknowledged.

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  1. Department of Chemistry, Hitit University, 19030, Corum, Turkey

    Sinan Basceken

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  1. Sinan Basceken
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Correspondence to Sinan Basceken.

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Basceken, S. Computational study of homogenous gold-catalyzed oxime–oxime rearrangement: Balci–Güven rearrangement. Struct Chem 31, 1765–1776 (2020). https://doi.org/10.1007/s11224-020-01531-x

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