Resolution of racemic mixtures of chiral arenechromiumtricarbonyl complexes using a Bakerbond Chiralcel HPLC column

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• 作者：Bitterwolf ; Thomas E. ; Hubler ; Timothy L.
• 关键词：Chromium ; Arene complexes ; High pressure liquid chromatography ; Chirality ; Chiral separation ; Arenechromiumtricarbonyl
• 刊名：Journal of Organometallic Chemistry
• 出版年：1995
• 出版时间：February 8, 1995
• 年：1995
• 卷：487
• 期：1-2
• 页码：119-125
• 全文大小：657 K

文摘

Racemic mixtures of eight new chiral arenechromiumtricarbonyl complexes were prepared and fully characterized by IR, ¹H and ¹³C NMR spectroscopy, mass spectrometry and elemental analysis. These compounds, along with 25 previously reported chiral complexes were used to establish the ability of commercially available chiral HPLC columns to effect resolution of the mixtures. It was found that Bakerbond Chiralcel OD® columns, consisting of derivatized cellulose on silica gel, successfully resolve racemic mixtures of most arene complexes with good to excellent results. Some tentative patterns in the effect of functional groups and ring substitution on the separation efficiency have been identified and are discussed. Direct resolution of complex 22, ethyl-ortho-methoxybenzoate Cr(CO)₃, was performed on the semipreparative scale. The resolved enantiomers were characterized by optical rotation measurements and gave the following data: band 1, t_R′1 = 77.8 min, [α]²¹₅₈₉ = + 30.0 ± 4.1°; band 2, t_R′2 = 179.8 min, [α]²¹₅₈₉ = −29.5 ± 1.0°.