查看“︁亚甲基三苯基膦”︁的源代码

{{Chembox
| verifiedrevid =
| ImageFile = Ph3P=CH2-ylid-phosphorane-resonance-2D.png
| ImageSize =
| ImageFile1 = Ph3P=CH2-from-xtal-1989-3D-balls.png
| PIN = Methylidenetri(phenyl)phosphane
| OtherNames =
|Section1={{Chembox Identifiers
| Abbreviations = 
| CASNo = 3487-44-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8GN8K95F62
| EINECS = 
| PubChem = 137960
| ChemSpiderID = 121606
| SMILES = C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
| InChI = 1/C19H17P/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h2-16H,1H2
| InChIKey = XYDYWTJEGDZLTH-UHFFFAOYAU
| StdInChI = 1S/C19H17P/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h2-16H,1H2
| StdInChIKey = XYDYWTJEGDZLTH-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = C<sub>19</sub>H<sub>17</sub>P
| Appearance = 黄色固体
| Density = 1.19 g/cm<sup>3</sup>
| Solubility =分解
 }}
}}
'''亞甲基三苯基膦'''是一種[[有機磷化合物]]，化學式<chem>Ph3PCH2</chem>。它屬於[[葉立德]]，可以作爲[[維蒂希試劑]]。

== 結構 ==
其晶體學表徵表示化合物中磷大約是[[四面体形分子构型|四面體構型]]，其中<chem>P=CH2</chem>部分呈[[平面分子構型|平面構型]]，而鍵長為1.661 Å。這比<chem>P-Ph</chem>鍵（1.823 Å）更短。<ref>{{cite journal |last1=Bart |first1=J. C. J. |year=1969 |title=Structure of the non-stabilized phosphonium ylid methylenetriphenylphosphorane |url=https://archive.org/details/sim_journal-of-the-chemical-society-b_1969_b_4/page/350 |journal=Journal of the Chemical Society B |volume=1969 |pages=350–365 |doi=10.1039/J29690000350}}</ref>

它有一對[[共振式]]：

Ph<sub>3</sub>P<sup>+</sup>CH<sub>2</sub><sup>−</sup> ↔ Ph<sub>3</sub>P=CH<sub>2</sub>

==合成與反應==
[[三苯基甲基溴化鏻]]和[[強鹼]]反應可以製備出亞甲基三苯基膦<ref>{{cite journal|doi = 10.1080/00397918508063883|title = The Wittig Reaction Using Potassium-tert-butoxide High Yield Methylenations of Sterically Hindered Ketones|year = 1985|last1 = Fitjer|first1 = Lutz|last2 = Quabeck|first2 = Ulrike|journal = Synthetic Communications|volume = 15|issue = 10|pages = 855–864}}</ref>：
:Ph<sub>3</sub>PCH<sub>3</sub>Br  +  BuLi  →  Ph<sub>3</sub>PCH<sub>2</sub>  +  LiBr  +  BuH

亦可以用[[苯基锂|苯基鋰]]與三苯基甲基溴化鏻在乾燥[[乙醚]]與[[氮氣]]流下反應製備而成。<ref>{{Cite book|title=基礎有機化學|url=https://archive.org/details/isbn_9787301272121_1|last=邢|first=其毅|year=2017|isbn=978-7-301-27212-1|location=北京|pages=[https://archive.org/details/isbn_9787301272121_1/page/644 644]|first2=偉偉|last2=裴|last3=徐|first3=瑞秋|last4=裴|first4=堅|chapter=第13章}}</ref>

而三苯基甲基溴化鏻可以由[[三苯基膦]]和[[溴甲烷]]反應製備而成，反應式如下：<ref>{{cite journal |last1=Fitjer |first1=Lutz |last2=Quabeck |first2=Ulrike |year=1985 |title=The Wittig Reaction Using Potassium-tert-butoxide High Yield Methylenations of Sterically Hindered Ketones |journal=Synthetic Communications |volume=15 |issue=10 |pages=855–864 |doi=10.1080/00397918508063883}}</ref>

:Ph<sub>3</sub>P + CH<sub>3</sub>Br → Ph<sub>3</sub>PCH<sub>3</sub>Br

作爲維蒂希試劑，它可以參與[[维蒂希反应|維蒂希反應]]<ref>{{cite journal
 | author = [[格奥尔格·维蒂希|Georg Wittig]], Ulrich Schöllkopf
 | journal =Chemische Berichte
 | year = 1954
 | volume = 87
 | pages = 1318
 | title = Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien I
 | doi = 10.1002/cber.19540870919}}</ref><ref>{{cite journal
 | author = Georg Wittig, Werner Haag
 | journal =Chemische Berichte
 | year = 1955
 | volume = 88
 | pages =  1654-1666
 | title = Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien II
 | doi = 10.1002/cber.19550881110}}</ref>，與[[酮]]、[[醛]]反應生成[[烯烃|烯烴]]，[[反应机理|反應機理]]如下：
[[File:Wittig Reaction Mechanism.png|center|500px|维蒂希反应机理]]
其中R1為氫。


== 應用 ==
亞甲基三苯基膦是[[有机合成|有機合成]]中常用的試劑。<ref>{{Cite journal |author1=B. E. Maryanoff |author2=A. B. Reitz |name-list-style=amp |year=1989 |title=The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects |journal=[[Chem. Rev.]] |volume=89 |issue=4 |pages=863–927 |doi=10.1021/cr00094a007}}</ref>以下為兩個亞甲基三苯基膦的應用實例：

[[File:Wittig_CH2_examples.png|center|450x450px|Two examples of the Wittig reaction using methylenetriphenylphosphorane]]另外亞甲基三苯基膦的[[维蒂希反应|維蒂希反應]]可應用於多烯類[[天然产物|天然產物]]的有機合成，例如[[麦角钙化醇|維生素D<sub>2</sub>]]的合成。<ref>{{Cite book|title=基礎有機化學|url=https://archive.org/details/isbn_9787301272121_1|last=邢|first=其毅|year=2017|isbn=978-7-301-27212-1|location=北京|pages=[https://archive.org/details/isbn_9787301272121_1/page/645 645]-646|first2=偉偉|last2=裴|last3=徐|first3=瑞秋|last4=裴|first4=堅|chapter=第13章}}</ref>


==參考資料==
{{reflist}}

[[Category:磷𬭩内盐]]
[[Category:苯基化合物]]