Chiral ferrocenylimine alcohols and corresponding reduced ferrocenyl secondary amine alcohols: synthesis, X-crystal structures and characterization

IF 1.6 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Transition Metal Chemistry Pub Date : 2024-08-30 DOI:10.1007/s11243-024-00604-8

Dan-Dan Lu, Ya-Meng Zhu, Yi-Jie Li, Ai-Quan Jia, Qian-Feng Zhang

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Abstract

Four ferrocenylimine alcohol compounds, [Fe(η⁵-C₅H₅){η⁵-C₅H₄CH=NCH(R)CH₂OH}] (R = Et, (R)-HL1, (S)-HL1; R = Bn, (R)-HL2, (S)-HL2), were synthesized by condensation reaction from ferrocenecarboxaldehyde and different chiral aminoalcohols. Reduction of HL1 and HL2 with sodium borohydride afforded four corresponding ferrocenyl secondary amine alcohol compounds, [Fe(η⁵-C₅H₅){η⁵-C₅H₄CH₂–NHCH(R)CH₂OH}] (R = Et, (R)-HL3, (S)-HL3; R = Bn, (R)-HL4, (S)-HL4). The crystal structures of (R)-HL1, (S)-HL1, (R)-HL2 and (S)-HL3·HCl were determined by single crystal X-ray diffraction. In addition, all compounds HL1–4 were characterized by ¹H NMR, ¹³C NMR, FT-IR, and UV–Vis spectroscopies.

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手性二茂铁亚胺醇和相应的还原二茂铁仲胺醇：合成、X 晶体结构和表征

通过二茂铁甲醛和不同手性氨基醇的缩合反应，合成了四种二茂铁亚胺醇化合物[Fe(η5-C5H5){η5-C5H4CH=NCH(R)CH2OH}]（R = Et，(R)-HL1，(S)-HL1；R = Bn，(R)-HL2，(S)-HL2）。用硼氢化钠还原 HL1 和 HL2 得到了四种相应的二茂铁基仲胺醇化合物 [Fe(η5-C5H5){η5-C5H4CH2-NHCH(R)CH2OH}] （R = Et，(R)-HL3，(S)-HL3；R = Bn，(R)-HL4，(S)-HL4）。通过单晶 X 射线衍射测定了 (R)-HL1、(S)-HL1、(R)-HL2 和 (S)-HL3-HCl 的晶体结构。此外，所有 HL1-4 化合物都通过 1H NMR、13C NMR、傅立叶变换红外光谱和紫外可见光谱进行了表征。

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来源期刊

Transition Metal Chemistry 化学-无机化学与核化学

CiteScore

3.60

自引率

0.00%

发文量

审稿时长

1.3 months

期刊介绍： Transition Metal Chemistry is an international journal designed to deal with all aspects of the subject embodied in the title: the preparation of transition metal-based molecular compounds of all kinds (including complexes of the Group 12 elements), their structural, physical, kinetic, catalytic and biological properties, their use in chemical synthesis as well as their application in the widest context, their role in naturally occurring systems etc. Manuscripts submitted to the journal should be of broad appeal to the readership and for this reason, papers which are confined to more specialised studies such as the measurement of solution phase equilibria or thermal decomposition studies, or papers which include extensive material on f-block elements, or papers dealing with non-molecular materials, will not normally be considered for publication. Work describing new ligands or coordination geometries must provide sufficient evidence for the confident assignment of structural formulae; this will usually take the form of one or more X-ray crystal structures.