Metal catalyzed rearrangement of a 2,2′-bipyridine Schiff-base ligand to a quaterpyridine-type complex

Wang, Jian; Onions, Stuart T.; Pilkington, Melanie; Stoeckli-Evans, Helen; Halfpenny, Joan; Wallis, John

doi:10.1039/b705555b

Cited by 15 publications

(21 citation statements)

References 16 publications

(22 reference statements)

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“…18 The 1 H and 13 C NMR spectra of 3 show characteristic 1 H and 13 C resonances at 8.34 and 162.3 ppm, respectively, consistent with the presence of an imine functionality. An intense band in the IR spectrum at 1630 cm −1 is assigned to the CN str of the bis-imine, shifted to slightly lower frequencies due to its conjugation with the pyridyl ring.…”

Section: Resultsmentioning

confidence: 81%

“…3,3′-Diamino-2,2′-bipyridine 1 and the Schiff-base bis-imine ligand 3 were synthesized following the methods described previously. 10,18 All chemicals were commercially available and used as received, unless otherwise stated.…”

Section: General Considerationsmentioning

confidence: 99%

“…The diverse reactivity of this ligand in the presence of Lewis acidic metal ions is not too surprising given that we previously isolated a complex of stoichiometry ĳCoĲ7)ĲOH 2 )ĲNCCH 3 )]ĲClO 4 ) 2 , from reaction of 3 with an excess of cobaltĲII) perchlorate. 18 In this case, instead of obtaining a diazapene heterocycle, a quaterpyridine type ligand was obtained comprising four contiguous heterocycles (three pyridines and one pyridoĳ2,3-d]pyrimidine) coordinated to the CoĲII) ion (Fig. 11).…”

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confidence: 99%

“…18 Schiff-base ligands are widely employed prepared from readily available starting materials and can incorporate N and/or O donors that can often result in compounds capable of binding metal ions in a multidentate manner.…”

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confidence: 99%

“…18 In order to probe this reactivity further, coordination complexes with transition metal ions were prepared, but single crystals of only two complexes were obtained for X-ray diffraction studies.…”

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Probing the reactivity of a 2,2′-bipyridyl-3,3′-bis-imine ligand by X-ray crystallography

et al. 2015

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The reactivity of a Schiff-base bis-imine ligand 3 is probed by X-ray diffraction studies. Its susceptibility to hydrolysis, oxidation and nucleophilic addition reactions is demonstrated by the isolation of the methanol adduct 4 and two diazapene heterocycles 5 and 6. This reactivity is also reflected in the molecular structures of two coordination complexes isolated by the reaction of 3 with MĲhfac) 2 salts, to afford ĳCuĲ5)-Ĳhfac)Ĳtfa)] (8) and ĳZnĲ6)Ĳhfac) 2 ] (9).

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Section: Resultsmentioning

confidence: 81%

Section: General Considerationsmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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