Optical resolution by molecular complexation chromatography

Klemm, L. H.; Reed, David

doi:10.1016/s0021-9673(01)97011-6

Cited by 62 publications

(14 citation statements)

References 6 publications

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“…In addition, the stepwiseness of this reaction leads to lose of stereospecificity, and it creates unwanted stereoisomers, such as enantiomers or diastereomers as their side products . On the other hand, development of those side products could bring along some problems and difficulties which are caused by some factors, such as expensive ingredients, high‐energy consumption, longer time, and more importantly the difficulties that appear in the subsequent efforts to separate or isolate the side products .…”

Section: Introductionmentioning

confidence: 99%

“…Although they have the same physical and chemical properties , the separation of the stereoisomers, either the enantiomer or the diastereoisomer, is usually a difficult, expensive, and time‐consuming task, as frequently reported by the researchers on organic synthesis. In most examples, the mechanism of the 1,3‐DC reaction is normally concerted and there is no medium in the reaction pathways ; therefore, by controlling several alternatives and applying them on the reaction conditions, the researcher could safely ensure the concertedness of the mechanism.…”

Section: Introductionmentioning

confidence: 99%

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The Effect of Position Replacement of Functional Groups on the Stepwise character of 1,3‐Dipolar Reaction of a Nitrile Oxide and an Alkene

Siadati

2016

Helvetica Chimica Acta

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It is a well-known fact that by changing the 1,3-dipolar cycloaddition (1,3-DC) reaction mechanism from concerted to stepwise, the stereospecificity is lost; since in synthesizing the required heterocyclic molecules that reaction is a requisite, it is important to study the concertedness of that reaction. Several papers on this subject have already stated that the existence of electron withdrawing groups (EWG) or electron donor groups (EDG) on dipole or dipolarophile leads to a high-energy differentiation between the dipole HOMO and dipolarophile LUMO (or vice versa) as well as the emergence of an intermediate in the reaction pathway. This paper seeks answering the question of when an EWG on dipole and an EDG on dipolarophile could be a factor in making the reaction mechanism stepwise, and does repositioning of functional groups in replacing dipole and dipolarophile switches the reaction mechanism from stepwise into concerted or vice versa?

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Effect of Position Replacement of Functional Groups on the Stepwise character of 1,3‐Dipolar Reaction of a Nitrile Oxide and an Alkene

Siadati

2016

Helvetica Chimica Acta

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“…The term complexation GC was introduced by Schurig [2], and the same technique is also called molecular complexation chromatography [3], charge-transfer type chromatography [4] and donoracceptor type complexation chromatography [5].…”

Section: Introductionmentioning

confidence: 99%

Quantitative relationship and application of 3‐benzylketoimine metal dichlorides in the analysis of volatile hydrocarbons

Wawrzyniak¹

2009

J of Separation Science

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Quantitative relationship and application of 3-benzylketoimine metal dichlorides in the analysis of volatile hydrocarbonsThe paper concerns the analysis of volatile hydrocarbons on newly designed and produced capillary columns. According to the type of coating used, the columns are of the PLOT type, and according to the adsorbate-adsorbent type interactions they belong to the category of complexation GC. The adsorbent used was silica, whose surface was modified with bonded 2-(3-triethoxysilylpropylimino)-3-(benzyl)-pentanone-4 to change the adsorption characteristics. The presence of the ketoimine group of strongly electron-accepting properties permitted the binding of transition metals. The metal ions are capable of interacting selectively with nucleophilic compounds including olefins. The transition metal ions used for sorbent modification were copper(II) chlorides and nickel(II) chlorides. The supported adsorbent was immobilised by bonding the modified silica to the column walls by a film of poly(dimethylsiloxane). Due to this strategy, the coating was very stable, no sorbent loss from the column was observed and the column could be washed with solvent. Besides exemplary separations, the paper quotes retention parameters of the group of compounds analysed and presents a discussion of the specific interactions between the adsorbate and adsorbent.

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“…This CSP has both K-acid (pnitrobenzyl) and K-base (naphthyl) functionality and is more predictable and capable of separating both K-acid and K-basic compounds. The earliest applications of charge-transfer (CT) complexation for optical resolution by LC was reported in the nineteen-sixties by Klemm and co-workers [15] and later by Mikeg and co-workers [16].…”

Section: Introductionmentioning

confidence: 99%

Direct resolution of the enantiomers of new diphosphine and diphosphine oxide ligands by high-performance liquid chromatography

et al. 2002

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Optical resolution by molecular complexation chromatography

Cited by 62 publications

References 6 publications

The Effect of Position Replacement of Functional Groups on the Stepwise character of 1,3‐Dipolar Reaction of a Nitrile Oxide and an Alkene

The Effect of Position Replacement of Functional Groups on the Stepwise character of 1,3‐Dipolar Reaction of a Nitrile Oxide and an Alkene

Quantitative relationship and application of 3‐benzylketoimine metal dichlorides in the analysis of volatile hydrocarbons

Direct resolution of the enantiomers of new diphosphine and diphosphine oxide ligands by high-performance liquid chromatography

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