Synthesis and structure of Cu(II) and Pd(II) coordination compounds with chiral α-thiooxime, a derivative of natural terpenoid (−)-α-pinene

Supramolecular arrangement promoted in trans-[PdCl2(HONC10H14O)2]·2H2O by hydrogen bonding

“…In particular we treated the [PdCl 2 (HONC 10 H 14 O) 2 ] complex with HCl and obtained an adduct of doubly hydrogen bonded water molecules that link both functionalities of the camphor ligand and the chloride atom of a symmetry related molecule. Structurally characterized palladium complexes with oxime ligands fall in two different categories as regards to their ability to promote supramolecular arrangements by hydrogen bonding: those with a bidentate chelating imine which crystallographically do not have hydrogen bonds such as 2-meth yl-2-nitroso-1-phenylpropan-1-one oxime-N,N 0 )-dichloro-palladium(II) [3] or 2-(benzylsulfanyl)-N-hydroxy-2,6,6-trimeth y lbicyclo[3.1.1]heptan-3-imine)-dichloro-palladium(II) [4] and those coordinated in a monodentate fashion which invariably depict inter-molecular hydrogen bonding linking the OH group of a molecule to the chloride of a symmetry related one. Examples of the later group are dichloro-bis(acetoxime) palladium [5], palladium(II) chloride bis(cyclohexanone oxime [6] or trans-bis(camphor oxime-N)-dichloro-palladium(II) [7].…”

Mannich-type three component condensation of α-substituted caran-4-one oximes with formaldehyde and secondary amines

“…4 N-Hydroxyimino derivatives (oximes) are poorly studied (if at all) as the C-H active component in the Mannich-type reaction. Chiral α-substituted oximes derived from natural terpenes are of great importance for coordination chemistry as polyheteroatomic ligands having an open-chain or cyclic topology of the set of donor atoms, [5][6][7][8] and Mannichtype condensation could be a prospective approach to the design of new polydentante ligands. Here we report on the first successful stereoselective introduction of an additional donor moiety into chiral α-substituted oximes by a three-component Mannich-type reaction.…”