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

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.