Ortho-(methylsulfanyl)phenylphosphonates and derivatives:
Synthesis and applications as mono- or bidentate ligands for
the preparation of platinum complexes

J 2013

Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes

KOZELKA, Jiří, Matthieu HAMEL, Matthieu LECINQ a MIhaela GULEA

Základní údaje

Originální název

Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes

Autoři

KOZELKA, Jiří (250 Francie, garant, domácí), Matthieu HAMEL (250 Francie), Matthieu LECINQ (250 Francie) a MIhaela GULEA (250 Francie)

Vydání

Journal of Organometallic Chemistry, Lausanne, Elsevier Science, 2013, 0022-328X

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10610 Biophysics

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.302

Kód RIV

RIV/00216224:14310/13:00070212

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1016/j.jorganchem.2013.07.069

UT WoS

000326112700030

Klíčová slova anglicky

Platinum complexes; Sigmatropic rearrangement; Bidentate ligands; Cis/trans isomerization

Štítky

AKR, rivok

Změněno: 8. 4. 2014 15:00, Ing. Andrea Mikešková

Anotace

V originále

The preparation of six phenylphosphonates (and phosphonic acid derivatives) bearing a sulfur group in ortho position was accomplished via either a [1,3]- or a [1,4]-sigmatropic rearrangement. Their complexation with different platinum sources has been studied and the new platinum complexes obtained were characterized by NMR spectroscopy (1H, 13C, 31P and 195Pt). Three runs of experiments were performed. The first was the reaction of ligands 1 and 2 bearing one sulfide and a phosphonate diester functions with potassium tetrachloroplatinate. In the obtained complexes, two molecules of ligand chelate the metal only by the sulfur atom. We were able to observe by 195Pt and 31P NMR spectroscopy the trans to cis rearrangement of a dichloro-methyl-(o-phosphorylbenzyl)sulfide platinum(II) complex upon time, leading to two new species, which are diastereomers of the cis-complex. The second set of experiments involved ligands 1, 2 and 3 bearing one sulfide or sulfoxide and a phosphonate diester moieties, cisplatin and one equivalent of silver nitrate. In the resulting complexes the platinum is coordinated by the sulfur atom of one molecule of ligand. In the third run, the reaction between ligands 4, 5, and 6 bearing one sulfide or sulfoxide and one phosphonic acid or one phosphonic monoester group and the cisplatin diaqua form led to O,SePt chelates.

Citovat

KOZELKA, Jiří, Matthieu HAMEL, Matthieu LECINQ a MIhaela GULEA. Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes. Journal of Organometallic Chemistry. Lausanne: Elsevier Science, 2013, roč. 745-746, NOV 15 2013, s. 206-213. ISSN 0022-328X. Dostupné z: https://dx.doi.org/10.1016/j.jorganchem.2013.07.069.

@article{1130254,
   author = {Kozelka, Jiří and Hamel, Matthieu and Lecinq, Matthieu and Gulea, MIhaela},
   article_location = {Lausanne},
   article_number = {NOV 15 2013},
   doi = {http://dx.doi.org/10.1016/j.jorganchem.2013.07.069},
   keywords = {Platinum complexes; Sigmatropic rearrangement; Bidentate ligands; Cis/trans isomerization},
   language = {eng},
   issn = {0022-328X},
   journal = {Journal of Organometallic Chemistry},
   title = {Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes},
   url = {http://dx.doi.org/10.1016/j.jorganchem.2013.07.069},
   volume = {745-746},
   year = {2013}
}

TY  - JOUR
ID  - 1130254
AU  - Kozelka, Jiří - Hamel, Matthieu - Lecinq, Matthieu - Gulea, MIhaela
PY  - 2013
TI  - Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes
JF  - Journal of Organometallic Chemistry
VL  - 745-746
IS  - NOV 15 2013
SP  - 206-213
EP  - 206-213
PB  - Elsevier Science
SN  - 0022328X
KW  - Platinum complexes
KW  - Sigmatropic rearrangement
KW  - Bidentate ligands
KW  - Cis/trans isomerization
UR  - http://dx.doi.org/10.1016/j.jorganchem.2013.07.069
N2  - The preparation of six phenylphosphonates (and phosphonic acid derivatives) bearing a sulfur group in ortho position was accomplished via either a [1,3]- or a [1,4]-sigmatropic rearrangement. Their complexation with different platinum sources has been studied and the new platinum complexes obtained were characterized by NMR spectroscopy (1H, 13C, 31P and 195Pt). Three runs of experiments were performed. The first was the reaction of ligands 1 and 2 bearing one sulfide and a phosphonate diester functions with potassium tetrachloroplatinate. In the obtained complexes, two molecules of ligand chelate the metal only by the sulfur atom. We were able to observe by 195Pt and 31P NMR spectroscopy the trans to cis rearrangement of a dichloro-methyl-(o-phosphorylbenzyl)sulfide platinum(II) complex upon time, leading to two new species, which are diastereomers of the cis-complex. The second set of experiments involved ligands 1, 2 and 3 bearing one sulfide or sulfoxide and a phosphonate diester moieties, cisplatin and one equivalent of silver nitrate. In the resulting complexes the platinum is coordinated by the sulfur atom of one molecule of ligand. In the third run, the reaction between ligands 4, 5, and 6 bearing one sulfide or sulfoxide and one phosphonic acid or one phosphonic monoester group and the cisplatin diaqua form led to O,SePt chelates.
ER  -

KOZELKA, Jiří, Matthieu HAMEL, Matthieu LECINQ a MIhaela GULEA. Ortho-(methylsulfanyl)phenylphosphonates and derivatives: Synthesis and applications as mono- or bidentate ligands for the preparation of platinum complexes. \textit{Journal of Organometallic Chemistry}. Lausanne: Elsevier Science, 2013, roč.~745-746, NOV 15 2013, s.~206-213. ISSN~0022-328X. Dostupné z: https://dx.doi.org/10.1016/j.jorganchem.2013.07.069.

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