The reaction of [(η6-p-cymene)RuCl(κ2N,O-L-serinate)], 1, with CH3C(O)Cl/NEt3, in chloroform at reflux temperature, led to the serendipitous isolation of the dehydroacetate complex [(η6-p-cymene)RuCl(κ2O,O′-dha)], 2, in low amount. Then, dehydroacetic acid (dhaH) was prepared in one pot by self condensation of acetyl chloride in the presence of NEt3 at room temperature, this reaction being unusual in the landscape of the chemistry of acyl chlorides. Complex 2 was synthesized in 89% yield from [(η6-p-cymene)RuCl2]2 and dhaH, and fully characterized by means of X-ray diffraction, IR and NMR spectroscopy. Complex 2 underwent fast and extensive dissociation of the dehydroacetate ligand in dmso/water solution, the degree of dissociation being substantially higher than that observed for the acetylacetonate ligand from [(η6-p-cymene)RuCl(κ2O,O′-acac)], 3.

One pot conversion of acetyl chloride to dehydroacetic acid and its coordination in a ruthenium(II) arene complex

Biancalana, Lorenzo;Pampaloni, Guido;Marchetti, Fabio
2017-01-01

Abstract

The reaction of [(η6-p-cymene)RuCl(κ2N,O-L-serinate)], 1, with CH3C(O)Cl/NEt3, in chloroform at reflux temperature, led to the serendipitous isolation of the dehydroacetate complex [(η6-p-cymene)RuCl(κ2O,O′-dha)], 2, in low amount. Then, dehydroacetic acid (dhaH) was prepared in one pot by self condensation of acetyl chloride in the presence of NEt3 at room temperature, this reaction being unusual in the landscape of the chemistry of acyl chlorides. Complex 2 was synthesized in 89% yield from [(η6-p-cymene)RuCl2]2 and dhaH, and fully characterized by means of X-ray diffraction, IR and NMR spectroscopy. Complex 2 underwent fast and extensive dissociation of the dehydroacetate ligand in dmso/water solution, the degree of dissociation being substantially higher than that observed for the acetylacetonate ligand from [(η6-p-cymene)RuCl(κ2O,O′-acac)], 3.
2017
Biancalana, Lorenzo; Pampaloni, Guido; Zacchini, Stefano; Marchetti, Fabio
File in questo prodotto:
File Dimensione Formato  
131 JOMC 2017.pdf

accesso aperto

Tipologia: Documento in Post-print
Licenza: Creative commons
Dimensione 343.28 kB
Formato Adobe PDF
343.28 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/877608
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 7
social impact