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Syntheses, spectroscopy and crystal structures of (R)-N-(1-Aryl-ethyl) salicylaldimines and [Rh{(R)-N-(1-aryl-ethyl)salicylaldiminato} (η4-cod)] complexes
Enamullah, Mohammed,Uddin, A. K. M. Royhan,Chamayou, Anne-Christine,Janiak, Christoph
, p. 807 - 817 (2007)
Condensation of salicylaldehyde with enantiopure (R)-(1-aryl-ethyl)amines yields the enantiopure Schiff bases (R)-N-(1-aryl-ethyl)salicylaldimine (HSB*; aryl = phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl (4), 4-bromophenyl (5), 2-naphthyl). These Schiff bases readily react with dinuclear (acetato)(η4-cycloocta-1,5-diene)rhodium(I), [Rh(μ-O2CMe)(η4-cod)]2, to afford the mononuclear complexes, cyclooctadiene-((R)-N-(1-aryl-ethyl)salicylaldiminato- κ2N,O)-rhodium(I), [Rh(SB*)(η4-cod)] (SB* = deprotonated chiral Schiff base = salicylaldiminate; aryl = phenyl (7), 2-methoxyphenyl, 4-methoxyphenyl, 4-bromophenyl, 2-naphthyl). The complexes have been characterized by IR, UV/vis, 1H/13C NMR and mass spectrometry, optical rotation as well as by single-crystal X-ray structure determination for 4, 5 and 7. The structure of 5 shows C-Br π contacts. Compound 7 is only the second example of a Rh(η4-cod) complex with a six-membered Rh-N,O-chelate ring.
