phosphorane

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/13 12:03:15」(JST)

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The structure of a typical phosphorane group.

A phosphorane (IUPAC name: λ⁵-phosphane) is a functional group in organophosphorus chemistry with pentavalent phosphorus. It has the general formula PR₅. The parent hydride compound is the unstable molecule PH₅. The derivative pentaphenylphosphorane (Ph₅P) is stable.

Phosphoranes adopt a trigonal bipyramidal molecular geometry with the two apical bonds longer than the three equatorial bonds. Hypervalent bonding is described by inclusion of non-bonding MOs, as also invoked for the closely related molecule phosphorus pentafluoride.

Phosphoranes of the type R₃P=CR₂ are more common and more important. Phosphoranes are also considered to be one of the resonance structures of ylides, these compounds feature a tetrahedral phosphorus center including a phosphorus–carbon double bond. These compounds are used as reagents in the Wittig reaction, for instance methylenetriphenylphosphorane or Ph₃P=CH₂.

See also

• Organophosphorus chemistry
• Phosphane

References

English Journal

• Isolation of a metastable geometrical isomer of a hexacoordinated dihydrophosphate: elucidation of its enhanced reactivity in umpolung of a hydrogen atom of water.

• Miyake H, Kano N, Kawashima T.SourceDepartment of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
• Inorganic chemistry.Inorg Chem.2011 Sep 19;50(18):9083-9. Epub 2011 Aug 23.
• Two of five conceivable geometrical isomers of a hexacoordinated dihydrophosphate bearing two sets of a bidentate ligand were investigated. X-ray crystallographic analysis of both of isomers, 1a-TPP and 1b-TEA, revealed their octahedral geometries of C(2) and C(1) symmetry, respectively, which were
• PMID 21861456

• An abridged transition state model to derive structure, dynamics, and energy components of DNA polymerase β fidelity.

• Klvaňa M, Jeřábek P, Goodman MF, Florián J.SourceDepartment of Chemistry, Loyola University Chicago, Chicago, Illinois 60626, United States.
• Biochemistry.Biochemistry.2011 Aug 16;50(32):7023-32. Epub 2011 Jul 25.
• We show how a restricted reaction surface can be used to facilitate the calculation of biologically important contributions of active site geometries and dynamics to DNA polymerase fidelity. Our analysis, using human DNA polymerase beta (pol β), is performed within the framework of an electrostatic
• PMID 21739967

Japanese Journal

• 高安定性リン複素環-重項ビラジカルおよび関連分子系の合成と性質

• 伊藤 繁和
• 有機合成化学協会誌 70(7), 731-741, 2012-07-01
• … Conversion into the cyclic phosphorane and thermal ring-expansion were facilitated by the presence of amino- and acyl substituents, respectively. …
• NAID 10030835420

• Martin-Lingandまたは拡張Martin-Ligandを有する6配位リン化合物の立体異性体

• 戸屋 裕也,姜 新東,小島 聡志,山本 陽介
• 基礎有機化学討論会要旨集（基礎有機化学連合討論会予稿集） 2011(0), 142-142, 2011
• Martin-Ligandまたは拡張Martin-Ligandを2つ有する6配位リン化合物の最安定構造を決定するため，アルキル単座配位子の位にフェニル基を2つ導入したスピロホスホランを合成し，塩基と反応させた。NMRによる反応追跡から拡張Martin-Ligand系では一種類のみの6配位リン化合物が確認でき，Martin-Ligand系では2種類の6配位リン化合物の異性体が確認できた。X線結晶構 …
• NAID 130004645637

• Z-Selective Horner-Wadsworth-Emmons-type Reaction Using a 10-P-5 Phosphorane Bearing Bidentates Derived from 1-Naphthol

• KOJIMA Satoshi,ARIMURA Jun-ya,KAJIYAMA Kazumasa
• Chemistry letters 39(11), 1138-1139, 2010-11-05
• NAID 10027315061

Related Links

• phosphorane - LookChem,look for chemicals all over the world.

Search LookChem database of chemicals Around the World:phosphorane. ... Product Names CAS Registry Number List of Suppliers

• Phosphorane | Referências na Internet | cyclopaedia.net

O termo Phosphorane é utilizado na Wikipedia de língua inglesa, onde se pode ler: A phosphorane (IUPAC name: λ 5-phosphane) is a functional group in organophosphorus chemistry with pentavalent phosphorus. It has the general ...

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