Univerzita Pardubice Fakulta chemicko- technologická

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Ferrocenyl derivatives of [1,2,3]-diazaphosphole and [1,2,3]-diazaarsole

Autoři: Kozáček Pavel | Dostál Libor | Růžička Aleš | Erben Milan

Rok: 2019

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	Ferrocenyl derivatives of [1,2,3]-diazaphosphole and [1,2,3]-diazaarsole	Diazaphospholes are well established compounds containing two nitrogen atoms, N(σ2,λ3) and N(σ3,λ3) together with one low-valent σ2,λ3-phosphorus atom incorporated in five-membered ring. On the contrary much less attention is given to diazaarsoles.1 The first representatives of ferrocene-substituted 2H-1,2,3-diazaphosphole and 2H-1,2,3-diazaarsole are described. The synthesis is based on the condensation of ferrocenylhydrazones with PCl3 or AsCl3 in the presence of triethylamine. The synthesis of 2H-diazaheterole (R = H) from corresponding hydrazones is successful only when ferrocenyl moiety is separated with suitable bridging group (e.g. -C6H4-, -CMe2-). Diazaheteroles with directly attached ferrocenyl substituent are available from 2-acetyl derivatives (R = Ac) which are formed in two-step reaction. Deacetylation of resulting heterocycles by phenylhydrazine or anhydrous hydrazine gives ferrocenyl substituted 2H-1,2,3-diazaheteroles in moderate yields. The newly synthetized compounds have been characterized by infrared, Raman and multinuclear (1H, 13C and 31P) NMR spectroscopy. Structures of several compounds have been confirmed by single-crystal X-ray diffraction analysis. The heterocyclic system obtained in this manner could be promising metallo-ligand with versatile coordination modes. It possesses both soft and hard donor atoms and, after deprotonation, it can be also considered as heteroaromatic analogue of cyclopentadienyl ligand.