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  9,9-Difluorobispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin

Mitra, R., Goddard, R., & Pörschke, K.-R. (2017). 9,9-Difluorobispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin. Inorganic Chemistry, 56(11), 6712-6724. doi:10.1021/acs.inorgchem.7b00836.

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 Creators:
Mitra, Raja1, Author              
Goddard, Richard2, Author              
Pörschke, Klaus-Richard1, Author              
Affiliations:
1Research Group Pörschke, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445616              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: As part of a comprehensive study of N-unsubstituted bispidines, the novel 9,9-difluorobispidine (D) has been synthesized. The compound crystallizes from pentane below 0 °C in the ordered-crystalline phase D-II and undergoes at 0–30 °C a stepwise endothermic phase transition to a dynamically disordered crystalline phase D-I; melting occurs at 227 °C. Single crystalline D-II has been subjected to X-ray structure analysis, revealing association of the molecules to form chains. Reaction of (1,5-hexadiene)PtCl2 with D affords {C7H10F2(NH)2}PtCl2 (D1), which can be converted by conventional routes to {C7H10F2(NH)2}Pt(cbdca)·5H2O (D2) and {C7H10F2(NH)2}Pt(C2O4) (D3). Compound D1 crystallizes solvent-free from water and is isomorphous to the solvent-free parent bispidine analogue (A1). The pentahydrate D2 is isomorphous to the bispidine and 9-oxabispidine homologues (A2 and C2), as shown by X-ray structure analyses. An increased polarity of the bispidine skeleton as a consequence of the high electronegativity of fluorine is seen as the reason for low cytotoxic potency of D1–D3.

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Language(s): eng - English
 Dates: 2017-03-312017-05-122017-06-05
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.inorgchem.7b00836
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Title: Inorganic Chemistry
  Abbreviation : Inorg. Chem.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 56 (11) Sequence Number: - Start / End Page: 6712 - 6724 Identifier: ISSN: 0020-1669
CoNE: https://pure.mpg.de/cone/journals/resource/0020-1669