On the Origin of the Conformationally Non-Interconvertable Isomers of Bisphenyldirhodium(III) Caprolactamate

Authors

  • Jian-Hua Xie University of Maryland
  • Michael P. Doyle University of Maryland

DOI:

https://doi.org/10.29356/jmcs.v53i3.997

Keywords:

Rhodium, Conformational Isomers, Acetic Acid, Phenylrhodium, Coupling

Abstract

A plausible explanation for the unprecedented formation of two conformational isomers of bisphenyldirhodium(III) caprolactamate is presented. The presence of acetic acid during the coupling process leading to the formation of bisphenyldirhodium(III) caprolactamate is shown to increase the propeller conformer at the expense of the biplanar conformer, Acetic acid is also found to catalyze the decomposition of bisphenyldirhodium(III) caprolactamate with the propeller conformation reacting at a rate that is more than ten times greater than that for the biplanar conformation. We speculate that protonation of one of the caprolactamate ligands changes the orientation of the phenyl ring in its approach to rhodium in the product-forming step of the arylation reaction leading to the formation of the two conformational isomers.

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Author Biographies

Jian-Hua Xie , University of Maryland

Department of Chemistry and Biochemistry

Michael P. Doyle, University of Maryland

Department of Chemistry and Biochemistry

References

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Published

2019-06-24

Issue

Vol. 53 No. 3 (2009): Special Issue of the J. Mex. Chem. Soc. in Honor of Dr. Ernest L. Eliel (1921-2008)

Section

Regular Articles

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