Oxidative halogenation of cisplatin and carboplatin: synthesis, spectroscopy, and crystal and molecular structures of Pt(IV) prodrugs
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Lippard_Oxidative halogenation.pdf
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953.28 KB
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5edeab825172eb02c9be3f408d7a2f92
Author(s)
Alexander, Sarah M.
Wilson, Justin J.
Lippard, Stephen J.
Johnstone, Timothy
Date Issued
October 2014
Journal
Dalton Transactions
Publisher
Royal Society of Chemistry, The
Citation
Johnstone, Timothy C., Sarah M. Alexander, Justin J. Wilson, and Stephen J. Lippard. “ Oxidative Halogenation of Cisplatin and Carboplatin: Synthesis, Spectroscopy, and Crystal and Molecular Structures of Pt(Iv) Prodrugs .” Dalton Trans. 44, no. 1 (2015): 119–129.
Version
Author's final manuscript
Abstract
A series of Pt(IV) prodrugs has been obtained by oxidative halogenation of either cisplatin or carboplatin. Iodobenzene dichloride is a general reagent that cleanly provides prodrugs bearing axial chlorides without the need to prepare intervening Pt(IV) intermediates or handle chlorine gas. Elemental bromine and iodine afford Pt(IV) compounds as well, although in the case of the iodine-mediated oxidation of carboplatin, an amido-bridged Pt(IV) side product also formed. A detailed analysis of the changes in spectroscopic and structural parameters induced by varying the axial halide is presented. A number of recurring motifs are observed in the solid state structures of these compounds.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1039/c4dt02627f
