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Upon the intriguing stereoselective formation of organobismuth(V) complexes

Barucki, Hubert; Coles, Simon J.; Costello, James F.; Hursthouse, Michael B.


Hubert Barucki

Simon J. Coles

Michael B. Hursthouse


The preparation of triphenyl-bismuth(v) 3a-k and antimony(v) 4e-k bis-carboxy ester complexes is described. A range of studies in solution suggest that the diastereoselective formation of (RR,SS)-3a-j is governed by the thermodynamic stability of rapidly interconverting epimeric species. Diastereoselectivity is absent in the case of the corresponding Sb complexes, leading to the conclusion that a combination of both ligand-ligand (steric) and metal-ligand (hyperconjugative) interactions govern stereoselectivity. The formation of homochiral complexes (RR,SS)-3a-j is rationalised using a simple model, invoking for the first time a palindromic BiPh3 propeller moiety, which correlates the chirality of the trans axial carboxy-ester ligands. The X-ray crystal structures of both hetero- and homochiral diastereoisomeric antimony complexes (4h and 4i, respectively) are presented in support of this model.


Barucki, H., Coles, S. J., Costello, J. F., & Hursthouse, M. B. (2003). Upon the intriguing stereoselective formation of organobismuth(V) complexes. Chemistry - A European Journal, 9(12), 2877-2884.

Journal Article Type Article
Publication Date Jun 16, 2003
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 9
Issue 12
Pages 2877-2884
Keywords antimony, bismuth, diastereoselectivity, hyperconjugation, propellers
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