Methyl phenyldiazoacetate

Methyl phenyldiazoacetate
Names
	Preferred IUPAC name Methyl diazo(phenyl)acetate
Identifiers
CAS Number	22979‐35‐7;
PubChem CID	53436974;
CompTox Dashboard (EPA)	DTXSID50700982 ;
Properties
Chemical formula	C9H8N2O2
Molar mass	176.175 g·mol−1
Appearance	yellow oil
Solubility in water	alkanes
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methyl phenyldiazoacetate is the organic compound with the formula C₆H₅C(N₂)CO₂Me. It is a diazo derivative of methyl phenylacetate. Colloguially 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]

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.[4]

References

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.

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[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: 1857–1869. doi:10.1039/C0CS00217H.

[2] Huw M. L. Davies; Wen‐hao Hu; Dong Xing. "Methyl Phenyldiazoacetate". eEROS. doi:10.1002/047084289X.rn00444.pub2.

[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: 1049–1059. doi:10.1021/om8007376.