Synthesis and characterisation of 1-alkyl-2-imidazoline complexes of noble metals; crystal structure of trans-[PtCl2{[upper bond 1 start]N[double bond, length as m-dash] C(H)N(Et)CH2C[upper bond 1 end]H2}(PEt3)] [hair space]

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Bekir Çetinkaya, Engin Çetinkaya, Peter B. Hitchcock, Michael F. Lappert and Ismail Özdemir


Abstract

Treatment of a 1-alkyl-2-imidazoline [upper bond 1 start]N(R)(CH2)2N[double bond, length as m-dash]C[upper bond 1 end]H with a µ-dichloro-dirhodium(I) or -diplatinum(II) complex [{Rh(µ-Cl)(cod)}2] or [{Pt(µ-Cl)Cl(PEt3)}2] gave the mononuclear 1-alkyl-2-imidazoline complex [RhCl{[upper bond 1 start]N[double bond, length as m-dash]C(H)N(R)CH2C[upper bond 1 end]H2 }(cod)] (R = Et 1a or CH2Ph 1b) or trans-[PtCl2{[upper bond 1 start]N[double bond, length as m-dash]C(H)N(R)CH 2C[upper bond 1 end]H2}(PEt3)] (R = Et 2a or CH2Ph 2b) (cod = cycloocta-1,5-diene). A single-crystal X-ray diffraction study of 2a revealed it to have a square-planar geometry about platinum, the imidazoline ring being coplanar with this plane, and a Pt–N distance of 2.088(11) Å; the Pt–P bond length of 2.231(4) Å indicates that the imidazoline ligand has a marginally stronger trans influence than analogues of its isomer such as [upper bond 1 start]CN(R)(CH2)2N[upper bond 1 end]R. The rhodium complexes 1a and 1b have been shown to catalyse cyclopropanation of styrene and ethyl diazoacetate in high yields.


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