Related Experiment Video
Updated: Jun 16, 2026
10:51
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
A practical and efficient method for the resolution of 3-phospholene 1-oxides via coordination complex formation
Viktória Ujj1, Péter Bagi, József Schindler
1Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary.
Chirality
|February 10, 2010
Summary
A novel method efficiently resolves phospholene oxides using chiral tartaric acid derivatives and metal ions. This crystallization technique yields optically active compounds, valuable for synthesizing tertiary phosphine oxides.
Area of Science:
- Organic Chemistry
- Chiral Synthesis
- Coordination Chemistry
Background:
- Chiral resolution of phospholene oxides is crucial for synthesizing enantiomerically pure compounds.
- Existing methods for phospholene oxide resolution can be complex or inefficient.
Purpose of the Study:
- To develop a simple, efficient, and economical method for resolving substituted 3-phospholene oxides.
- To explore the use of chiral tartaric acid derivatives and metal ions in diastereomeric complex formation for chiral resolution.
Main Methods:
- Utilized o,o'-dibenzoyl- or o,o'-di-p-toluyl-(2R,3R)-tartaric acid derivatives.
- Employed calcium or magnesium ions to form crystalline diastereomeric coordination complexes with phospholene oxides.
- Separated enantiomers via crystallization and digestion of the formed complexes.
- Analyzed thermal behavior using simultaneous Thermogravimetric Differential Thermal Analysis (TG/DTA).
Main Results:
- Successfully developed a method for resolving phospholene oxides.
- Formed crystalline diastereomeric coordination complexes between metal salts of tartaric acid derivatives and phospholene oxides.
- Obtained optically active phospholene oxides through crystallization and digestion of these complexes.
- Demonstrated the thermal stability of the diastereomeric complexes.
Conclusions:
- The developed method provides an efficient and economical route for obtaining optically active phospholene oxides.
- This approach shows potential for broader application in the resolution of tertiary phosphine oxides.
- The combination of chiral recognition and coordination chemistry offers a powerful tool for chiral separations.
Related Concept Videos
01:14Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
02:54Coordination Compounds and Nomenclature
In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
03:00Preparation of Epoxides
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
02:42Valence Bond Theory
Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
03:08Hydroboration-Oxidation of Alkenes
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.