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Methyl phenyldiazoacetate

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Methyl phenyldiazoacetate
Names
Preferred IUPAC name Methyl diazo(phenyl)acetate
Identifiers
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula C9H8N2O2
Molar mass 176.175 g·mol
Appearance Yellow oil
Solubility in alkanes Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. Methyl phenyldiazoacetate is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.

Solid state structure of t-BuO2CC(N2)C6H4NO2, a representative donor-acceptor carbene related to the title compound. Key distances: C-N = 1.329 Å, N-N = 1.121 Å.

References

  1. 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 (4): 1857–1869. doi:10.1039/C0CS00217H. PMID 21359404.
  2. Huw M. L. Davies; Wen-hao Hu; Dong Xing (2015). "Methyl Phenyldiazoacetate". EEROS: 1–10. doi:10.1002/047084289X.rn00444.pub2. ISBN 978-0-470-84289-8.
  3. 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.
  4. 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 (4): 1049–1059. doi:10.1021/om8007376.
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