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Some plant oil derived cyclohexane tricarboxylic acid triesters were synthesized and suggested as potential plasticizers based mainly on renewable feedstock. Methyl calendulate 1 and α-eleostearate 2 obtained from calendula oil and tung oil, respectively, as well as methyl oleate 3 were used as starting material. Reactions with maleic anhydride gave the corresponding Diels-Alder adducts 4 and 5 and ene adduct 6, which were converted by ring-opening reactions with various alcohols to the respective tricarboxylic acid triesters. Especially the cyclohexane tricarboxylic trimethyl triester 9 derived from Diels-Alder adduct 5 showed excellent absorption properties by PVC, superior to bis(2-ethylhexyl)phthalate (DEHP). Moreover, the commercially available Diels-Alder adduct of CLA 7 (Admergin acid") was ring-opened with methanol showing an absorption by PVC that was still higher compared to triester 9 although the viscosity was significantly higher.

The following known and novel cobalt carbonyl complexes are formed by reactions of cobalt metal with bipy, phen, Ph2P-CH2-CH2-PPh2 (P͡P), PPh3, Ph2P-CH2-CH2-NEt2 (P͡N), InCl, SnX2 (X = Cl, Br, I), Cd and HgBr2 under CO pressure (200 bar): [Co(bipy)3][Co(CO)4]2, [Co(phen)3][Co(CO)4]2, [Co2(P͡P)3(CO)4][Co(CO)4]2; Co2(CO)6 (PPh3)2, Co2(CO)6 (P͡N)2; [Co(CO)4]2SnCl2, {[Co(CO)4]2InCl}2; [Co(CO)3PPh3]2SnX2(X = Cl, Br, I), [Co(CO)3(P͡N)]2SnCl2, [Co(CO)3(P͡N)]2M (M = Cd, Hg).

The reactions of the cationic complexes [η5-C5H5M(CO)3]+ (M = Fe, Ru, Os), [η5-C5H5Ru(CO)2(L)]+ (L = MeNC, PPh3, PEt3), {[η5-C5H5Ru(CO)2]2(Ph2PCH2CH2PPh2)}2+ and of the covalent carbamoyl carbonyl compounds η5-C5H5M(CO)2(CONH2) (M = Fe, Ru, Os), η5-C5H5Ru(CO)(L)(CONH2) (L = MeNC, PPh3, PEt3), [η5-C5H5Ru(CO)(CONH2)]2(Ph2PCH2CH2PPh2) with liquid NH3 above 10 C° yield the hydrido carbonyls η5-C5H5M(CO)2(H), η5-C5H5Ru(CO)(L)(H) and [η5-C5H5Ru(CO)(H)]2(Ph2PCH2CH2PPh2) with the simultaneous formation of NH4NCO or CO(NH2)2.

By treatment of Co2(CO)8 with 1-diphenylphosphino-2-diethylaminoethane, Ph2P-CH2-CH2-NEt2 (P͡N), [Co(CO)3(P͡N)2][Co(CO)4] or Co2(CO)6(P͡N)2 are formed, depending on the reaction conditions. The complex Co2(CO)4 (nor-C7H8)2 also reacts with P͡N to give the substituted cobalt carbonyl Co2(CO)6(P͡N)2. Insertion of SnCl2 and the II B group metals into the Co-Co bond is possible.

The covalent carbamoyl compounds M(CO)2(PR3)2(Hal)(CONH2) (M = Fe, Ru, Os; Hal = Cl, Br; R = Ph, Cyclohexyl) and Os(CO)(NO)(PPh3)2(CONH2) are formed by the reactions of the cationic complexes [M(CO)3(PR3)2(Hal)]+ and [Os(CO)2(NO)(PPh3)2]+ with liquid NH3 between -75 and -40 °C.

The crystal structure of the monoclinic η5-C5H5RU(CO)2(CONH2) has been determined by X-ray diffraction (space group P1̄ with Z - 4 and a = 1248,3 pm, b = 963,3 pm, c = 845,2 pm, α= 97,35°, β= 106,11°, and γ= 99,32°). The Ru is pseudo-octahedrally coordinated to the η5-C5H5 ring, the two CO groups and the CONH2 ligand with a planar RuC(O)N-moiety. Dimers are formed by N-H···O hydrogen bonds connecting the carbamoyl ligands of two molecules. Further hydrogen bonds link these dimers to form a helical chain.

The covalent carbamoyl compounds η5-C5H5Ru(CO)(L)(CONH2) (L = CO, MeCN, MeNC, PPh3, PEt3) and η5-C5H5Os(CO)2(CONH2) are formed by the reactions of the cationic complexes [η5-C5H5Ru(CO)2(L)]+ (L = CO, MeCN, MeNC, PPh3, PEt3) and [η5-C5H5Os(CO)3]+ with liquid NH3 below 10 °C. In contrast, the reaction of [η5-C5H5Ru(CO)2(η2-C2H4)]PF6 with liquid NH3 yields the quarternary ammonium salt [η5-C5H5Ru(CO)2(CH2CH2 ⊕NH3)]PF6. With the cationic complexes {[η5-C5H5M(CO)2]2(P̑P)}++ (M = Fe, Ru; P̑P = Ph2PCH2CH2PPh2) it was possible to prepare the dinuclear P̑P bridged carbamoyl derivatives [η5-C5H5M(CO)(CONH2)]2(P̑P).

The syntheses and the IR and 1H NMR spectra of the new cations [ƞ5-C5H5Ru(CO)2L]+(L=CH3CN, propene, cyclohexene, PPh3, PEt3, NH3,CNCH3) , {[ƞ5-C5H5Ru(CO)2]2PP}2+ and [ƞ5-C5H5Ru(CO)PP]+ (PP=Ph2PCH2CH2PPh2) are described.