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Organometallic Complexes of Iridium, Palladium, Chromium and Iron from 2‐Phenyl‐5(4 H )‐oxazolones − Organometallic Labelled Dipeptides
Author(s) -
Bauer Werner,
Prem Markus,
Polborn Kurt,
Sünkel Karlheinz,
Steglich Wolfgang,
Beck Wolfgang
Publication year - 1998
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199804)1998:4<485::aid-ejic485>3.0.co;2-y
Subject(s) - chemistry , oxazolone , palladium , adduct , organometallic chemistry , bimetallic strip , medicinal chemistry , deprotonation , amide , group 2 organometallic chemistry , dipeptide , iridium , chromium , stereochemistry , catalysis , peptide , organic chemistry , ion , molecule , biochemistry
Reactions of 2‐phenyl‐4‐R‐5(4 H )‐oxazolones (R = Me, CH 2 Ph, CHMeEt) with [(η 5 ‐C 5 Me 5 )IrCl 2 ] 2 afforded the cyclometallated complexes (η 5 ‐C 5 Me 5 )(Cl)Ir(L) ( 1 − 3 ) [L = 2‐phenyl‐4‐R‐5(4 H )‐oxazolone( C ‐ o , N )]. 2‐Phenyl‐5(4 H )‐oxazolone reacts with [(η 5 ‐C 5 Me 5 )IrCl 2 ] 2 and palladium(II) acetate to give complexes with a C ‐ o , N ‐bridging oxazolone [(η 5 ‐C 5 Me 5 )(Cl)Ir] 2 (μ‐Cl)(μ‐L‐H + ) ( 4 ) and Pd 3 (μ‐ac) 5 (μ‐L‐H + ) ( 5 ). 2‐Phenyloxazolone anions were added to the π ligands of [(η 5 ‐C 6 H 7 )Fe(CO) 3 ] + and [(η 7 ‐C 7 H 7 )Cr(CO) 3 ] + to give the adducts 6 − 11 . Dipeptide derivatives 12 − 18 were obtained by reaction of 1 , 2 and by reaction of the adduct 6 from [(η 5 ‐C 6 H 7 )Fe(CO) 3 ] + ; and the anion of 2‐phenyloxazolone with α‐amino acid esters. These reactions may be used for the labelling of peptides. Saponification of 15 − 18 yields the organometallic substituted peptide acids 19 − 22 . Their dianions (deprotonation of COOH and peptide amide) were used as ligands towards (Ph 3 P) 2 PtCl 2 to yield the bimetallic complexes 23 − 25 . The structures of 4 , 5 , 9 and 10 were determined by X‐ray diffraction.