New chiral organoantimony(iii) compounds containing intramolecular N → Sb interactions - Solution behaviour and solid state structures

Article abstract of DOI:10.1039/c003318a

Hypervalent organoantimony(iii) compounds of the type [2-(Me ₂NCH₂)C₆H₄]PhSbCl (1), [2-(Me ₂NCH₂)C₆H₄]MesSbBr (7) and [2-(Me₂NCH₂)C₆H₄]_nAr _3-nSb [n = 1, Ar = Ph (4), Mes (9); n = 2, Ar = Ph (5), Mes (10)] were prepared via salt elimination reactions between [2-(Me₂NCH ₂)C₆H₄]Li and MesMgBr and Ph _nSbCl_3-n, [2-(Me₂NCH₂)C ₆H₄]SbBr₂ or [2-(Me₂NCH ₂)C₆H₄]_nSbCl_3-n (n = 1, 2), in appropriate molar ratios. Halogen exchange reactions with aqueous KBr or KI gave [2-(Me₂NCH₂)C₆H₄]ArSbX [Ar = Ph, X = Br (2), I (3); Ar = Mes, X = I (8)]. Metathesis reaction between 1 and MesMgBr affords [2-(Me₂NCH₂)C₆H ₄]PhMesSb (6). Compounds 1-10 were investigated by means of NMR (¹H, ¹³C) in solution and by mass spectrometry. The investigation of the molecular structures of 2-8 by single-crystal X-ray diffraction revealed that the nitrogen atoms of the pendant CH ₂NMe₂ arms are strongly coordinated to the antimony atoms. All compounds exhibit chirality and crystallize as racemic mixtures. The Royal Society of Chemistry.