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CN: 11-1818/O6
University Chemistry
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Recent Advances in the Synthesis of Organic Phosphorus Compounds
via
Activation of Inorganic White Phosphorus
Fengxiao Wang, Zhiwei Miao
University Chemistry 2024, 39 (
12
): 185 -201. DOI:
10.12461/PKU.DXHX202404063
Abstract
(
2623
)
Full text @ ScienceDirect
Knowledge map
Organic phosphorus compounds play a crucial role in various fields, including organic chemistry, agriculture, and materials science. White phosphorus (P
4
) is a key raw material in the modern phosphorus chemical industry and serves as a common source of phosphorus atoms for the synthesis of organic phosphorus compounds. In recent years, researchers have focused on exploring the chemical properties of white phosphorus with the aim of developing methods for the direct conversion of inorganic white phosphorus into phosphorus-containing functional compounds. This approach not only circumvents the multi-step traditional processes currently employed in the phosphorus chemical industry but also contributes to environmental protection and cost reduction. This article reviews the recent advancements in the direct synthesis of organic phosphorus compounds from inorganic white phosphorus and discusses the future prospects for development in this area.
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The Evolution and Current Status of Organophosphorus Pesticides
Junyuan Zhang, Zhiwei Miao
University Chemistry 2025, 40 (
6
): 129 -138. DOI:
10.12461/PKU.DXHX202408118
Abstract
(
3056
)
Full text @ ScienceDirect
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Organophosphorus pesticides are a critical class of agricultural chemicals that play a significant role in pest and disease control and in enhancing crop yields. However, their widespread use has also led to serious environmental concerns and potential health risks, prompting the ban and discontinuation of many products. Despite these challenges, organophosphorus pesticides continue to be favored for their high efficiency, low cost, and ease of production. A few types remain essential in agricultural practices, particularly in less-developed regions where their use still holds potential for growth. This article provides a comprehensive review of the development, current status, and future prospects of organophosphorus pesticides.
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Synthesis and Application of the Chiral Ferrocenyl Diphosphine Ligand Xyliphos
Guilan He, Yaofeng Yuan
University Chemistry 2025, 40 (
8
): 130 -137. DOI:
10.12461/PKU.DXHX202409122
Abstract
(
3175
)
Full text @ ScienceDirect
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Chiral ferrocenyl diphosphine ligands are widely used in asymmetric catalysis, with Xyliphos being one of the most prominent examples. The iridium complex of Xyliphos is employed in the asymmetric hydrogenation of MEA (2-methyl-6-ethylaniline)-imide, a key intermediate in the enantioselective synthesis of the chiral herbicide (
S
)-metolachlor. This catalytic process is highly efficient, achieving a turnover rate exc
ee
ding 2,000,000, with an annual production capacity surpassing 10,000 tons. It is the largest-scale enantioselective catalytic process demonstrated to date. The synthesis and successful industrial application of Xyliphos represent a significant milestone, highlighting the successful transition from basic research to industrial implementation, with profound and far-reaching implications.
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Academician Chengye Yuan and Organic Phosphorus Chemistry
Shuai Yuan, Yaofeng Yuan
University Chemistry 2025, 40 (
7
): 393 -400. DOI:
10.12461/PKU.DXHX202409123
Abstract
(
2432
)
Full text @ ScienceDirect
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Yuan Chengye is the pioneer in the field of extractant chemistry in China. In response to national defense needs such as the “Two Bombs, One Satellite” program, he successfully developed key extractants, including P204 (bis(2-ethylhexyl)phosphoric acid ester) and P350 (methylphosphonic acid dimethylheptyl ester). He also developed various phosphorus extractants, such as P507 (2-ethylheptylphosphonic acid-2-ethylheptyl ester), based on the comprehensive utilization of non-ferrous metals. Mr. Yuan Chengye’s team conducted extensive research on the structure and performance of extractants, based on a large amount of experimental data. Through in-depth analysis using quantum chemistry, molecular mechanics, thermodynamics, and other testing methods, they enhanced the chemical properties of organic phosphorus extractants to a new level. These studies provide a solid theoretical foundation for the design and optimization of extractants and have also advanced industrial applications.
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Recent Advances in Low-Coordinated Phosphorus-Containing Functional Groups
Wen Jiang, Jieli Lin, Zhongshu Li
University Chemistry 2025, 40 (
8
): 138 -151. DOI:
10.12461/PKU.DXHX202409144
Abstract
(
2252
)
Full text @ ScienceDirect
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Functional groups are essential molecular building blocks that govern the physicochemical properties of molecules. The study of their structure, properties, and functions is central to synthetic chemistry, forming the foundation of modern synthetic chemistry theories. In the pursuit of discovering and creating new substances, the design and development of novel functional groups is of particular importance. With advancements in synthetic technology, new functional groups containing main-group elements such as phosphorus (P), boron (B), sulfur (S), and silicon (Si) have been reported. According to the diagonal rule, phosphorus-containing functional groups can exhibit properties similar to their carbon-containing counterparts. Moreover, the introduction of phosphorus atoms can further modulate the steric and electronic properties of these groups, revealing distinctive physicochemical characteristics and broad application potential. This review summarizes recent developments in low-coordinated phosphorus-containing functional groups, such as phosphaalkynes, diphosphorus compounds, phosphinidenes, phosphaalkenes, diphosphenes, and phosphinines, and discusses the future directions for research in this field.
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Organophosphorus Chemistry and Its Integration in Teaching of Chemistry
Fengxiao Wang, Zhiwei Miao, Yaofeng Yuan
University Chemistry 2025, 40 (
8
): 158 -168. DOI:
10.12461/PKU.DXHX202410077
Abstract
(
3214
)
Full text @ ScienceDirect
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As vital constituents of organoelemental compounds, organophosphorus compounds find extensive applications across diverse fields including materials science, agrochemicals, and organic synthesis, demonstrating significant relevance to daily life. While phosphorus, as a crucial main-group element, is introduced with its fundamental properties in secondary education, undergraduate chemistry curricula primarily emphasize more advanced inorganic phosphorus chemistry with limited coverage of organophosphorus chemistry. This article highlights recent research advances in organophosphorus chemistry and proposes pedagogical considerations for incorporating organophosphorus chemical knowledge into undergraduate teaching.
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Selection of Phosphorus Sources and Synthesis of Three Phosphorus-Containing Flame Retardants with Evaluation of Their Flame Retardant Performance
Ruilan Fan, Xiaoling Huang
University Chemistry 2025, 40 (
8
): 181 -191. DOI:
10.12461/PKU.DXHX202410025
Abstract
(
3849
)
Full text @ ScienceDirect
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The choice of phosphorus source compounds plays a pivotal role in the synthesis of phosphorus-based flame retardants. In addition to evaluating flame retardant efficiency, critical parameters such as chemical reactivity, thermal stability, and economic feasibility must be carefully considered. This study presents a comparative analysis of three distinct phosphorus sources: phosphorus oxychloride, hexachlorocyclotriphosphazene, and phytic acid, highlighting their respective advantages and limitations. Furthermore, we detail the synthetic procedures for three phosphorus-containing flame retardants and demonstrate their effectiveness in enhancing the flame resistance of polyurethane materials. These findings offer valuable guidance for the judicious selection of phosphorus sources in flame retardant design. The presented chemical reactions and characterization methodologies also serve as practical extensions to fundamental organic chemistry curricula, facilitating students’ comprehension of theoretical concepts through their application in research contexts.
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The Stereoselectivity of the Wittig Reactions
Zhi Chai, Huashan Huang, Xukai Shi, Yujing Lan, Zhentao Yuan, Hong Yan
University Chemistry 2025, 40 (
8
): 192 -201. DOI:
10.12461/PKU.DXHX202410046
Abstract
(
5737
)
Full text @ ScienceDirect
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The Wittig reaction is a well-established method for synthesizing olefins. However, undergraduate organic chemistry textbooks often provide only a cursory overview of the mechanisms and stereoselectivities associated with these reactions. This article aims to enhance the existing literature by introducing several proposed mechanisms of the Wittig reaction and their corresponding explanations for stereoselectivity. It is our hope that this discussion will aid students in understanding the mechanisms and stereoselective outcomes of the Wittig reaction, thereby reinforcing their foundational knowledge of organic chemistry.
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