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Synthesis of Mono‐, Di‐, and Tri‐arylgold(III) Complexes Using Organomercury Compounds – Synthesis of the First Aurated Schiff Bases
Author(s) -
Vicente Jose,
Berm údez MaríaDolores,
Carri ón FranciscoJosé,
Jones Peter G.
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961291025
Subject(s) - chemistry , stereochemistry , adduct , medicinal chemistry , organic chemistry
The formylarylmercury(II) complex [Hg{C 6 H(CHO)‐6‐(OMe) 3 ‐2,3,4} 2 ] reacts with 4‐butylaniline (1:2) to give [Hg{C 6 H(CH=NC 6 H 4 C 4 H 9 ‐4′)‐6‐(OMe) 3 ‐2,3,4} 2 ] ( 1 ) by a condensation reaction. This complex reacts with Me 4 ‐N[AuCl 4 ] (1:1) to give [Hg{C 6 H(CH=NC 6 H 4 C 4 H 9 ‐4′)‐6‐(OMe) 3 ‐2,3,4}Cl] ( 2 ) and the monoarylgold(III) compound cis ‐C 6 H 4 ‐ n Bu‐4′)‐6‐(OMe) 3 ‐2,3,4}Cl 2 ] ( 3 ). This complex reacts with PPh 3 (1:1) to give the adduct cis ‐[Au{C 6 H(CH=NC 6 H 4 ‐ n , Bu‐4′)‐6‐(OMe) 3 ‐2,3,4}Cl 2 (PPh 3 )] ( 4 ) and with AgClO 4 (1:1) in acetone to give the ketonyl complex cis ‐[C 6 H 4 ‐ n Bu‐4′)‐6‐ (OMe) 3 ‐2,3,4}‐{CH 2 C(O)Me}Cl] ( 5 ). cis ‐Me 4 N[Au(C 6 H 4 NO 2 ‐2) 2 Cl 2 ] react with [Hg{C 6 H 3 (N=NC 6 H 4 OMe‐4′)‐2‐(OMe)‐5}Cl] and Me 4 NCl (1:1:1) to give cis ‐[C 6 H 4 OMe‐4′)‐2‐ (OMe)‐5}(C 6 H 4 NO 2 ‐2) 2 ] ( 6 ): Similarly, cis ‐Me 4 N‐[Au(C 6 H 4 CF 3 ‐2) 2 Cl 2 ] ( 7 ), obtained by treating [Hg(C 6 H 4 CF 3 ‐2) 2 ] with Me 4 N[AuCl 4 ] and Me 4 NCl (1:1:1), reacts with [Hg(C 6 H 4 CH 2 NMe 2 ‐2)Cl] and Me 4 NCl (1:1:1) to give the triarylgold(III) complex cis ‐[Me 2 ‐2)(C 6 H 4 CF 3 ‐2) 2 ] ( 8 ). This complex can also be obtained by treating cis ‐[Me 2 ‐2)Cl 2 ] with [Hg(C 6 H 4 CF 3 ‐2) 2 ] and Me 4 NCl (1:1:1). The crystal structure of 3 reveals the presence of two independent molecules, in one of which the butylphenyl group is disordered. The geometry at the gold atom is square planar; distortions may be attributed to the narrow bite angle and steric repulsion between a chloride ligand and the ortho ‐methoxy group. The greater trans influence of the aryl ligand causes a great difference in Au–Cl bond lengths.