Methyl phenyldiazoacetate
Appearance
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Names | |
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Preferred IUPAC name
Methyl diazo(phenyl)acetate | |
Identifiers | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C9H8N2O2 | |
Molar mass | 176.175 g·mol−1 |
Appearance | Yellow oil |
Solubility in alkanes | Soluble |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl phenyldiazoacetate is the organic compound with the formula C6H5C(N2)CO2Me. It is a diazo derivative of methyl phenylacetate. Colloquially referred to as "phenyldiazoacetate", it is generated and used in situ after isolation as a yellow oil.
Methyl phenyldiazoacetate and many related derivatives are precursors to donor-acceptor carbenes, which can be used for cyclopropanation or to insert into C-H bonds of organic substrates. These reactions are catalyzed by dirhodium tetraacetate or related chiral complexes.[1] Methyl phenyldiazoacetate is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.[2][3]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/6/6c/DOXGON.png/220px-DOXGON.png)
References
[edit]- ^ Davies, H. M. L.; Morton, D. (2011). "Guiding Principles for Site Selective and Stereoselective Intermolecular C–H Functionalization by Donor/Acceptor Rhodium Carbenes". Chemical Society Reviews. 40: 1857–1869. doi:10.1039/C0CS00217H.
- ^ Huw M. L. Davies; Wen‐hao Hu; Dong Xing. "Methyl Phenyldiazoacetate". eEROS. doi:10.1002/047084289X.rn00444.pub2.
- ^ Selvaraj, Ramajeyam; Chintala, Srinivasa R.; Taylor, Michael T.; Fox, Joseph M. (2014). "3-Hydroxymethyl-3-phenylcyclopropene". Org. Synth. 91: 322. doi:10.15227/orgsyn.091.0322.
- ^ Shishkov, I. V.; Rominger, F.; Hofmann, P. (2009). "Remarkably Stable Copper(I) α-Carbonyl Carbenes: Synthesis, Structure, and Mechanistic Studies of Alkene Cyclopropanation Reactions". Organometallics. 28: 1049–1059. doi:10.1021/om8007376.