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Nucleophilic substitution at phosphorus: stereochemistry and mechanisms

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<![CDATA[<ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="graphical" xml:lang="en" id="ab005" view="all"><ce:section-title id="st005">Graphical abstract</ce:section-title><ce:abstract-sec id="as005" view="all"><ce:simple-para>Display Omitted</ce:simple-para></ce:abstract-sec></ce:abstract><ce:abstract xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns="http://www.elsevier.com/xml/ja/dtd" class="author" xml:lang="en" id="ab010" view="all"><ce:section-title id="st010">Abstract</ce:section-title><ce:abstract-sec id="as010" view="all"><ce:simple-para id="sp0010" view="all">This review is devoted to the stereochemistry of nucleophilic substitution reactions at phosphorus. The study of the reactions of phosphoryl group transfer is important for biological and molecular chemistry. The stereochemistry and mechanisms of S<ce:inf loc="post">N</ce:inf>1(P) monomolecular and S<ce:inf loc="post">N</ce:inf>2(P) bimolecular nucleophilic substitution reactions of organophosphorus compounds are discussed. It has been shown that hydrolysis of many natural phosphates proceeds according to the monomolecular S<ce:inf loc="post">N</ce:inf>1(P) mechanism via the formation of metaphosphate intermediate (PO<ce:inf loc="post">3</ce:inf><ce:sup loc="post">?</ce:sup>). S<ce:inf loc="post">N</ce:inf>2(P) nucleophilic substitution at chiral trivalent or pentavalent phosphorus compounds proceeds via the formation of penta-coordinated transition state or pentacoordinate intermediate.</ce:simple-para></ce:abstract-sec></ce:abstract>]]>

Oleg I. Kolodiazhnyi、Anastasy Kolodiazhna

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Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine

2017

Tetrahedron, Asymmetry

Tetrahedron, Asymmetry

ISSN:0957-4166
年,卷(期):2017.28(12)
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