Methyl phenyldiazoacetate explained

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]}

Notes and References

1. Davies, H. M. L.. Morton, D.. Guiding Principles for Site Selective and Stereoselective Intermolecular C–H Functionalization by Donor/Acceptor Rhodium Carbenes. Chemical Society Reviews. 2011. 40. 4 . 1857–1869. 10.1039/C0CS00217H. 21359404 .
2. Methyl Phenyldiazoacetate. Huw M. L. Davies. Wen-hao Hu. Dong Xing. EEROS. 2015 . 1–10 . 10.1002/047084289X.rn00444.pub2. 978-0-470-84289-8 .
3. 3-Hydroxymethyl-3-phenylcyclopropene. Ramajeyam. Selvaraj. Srinivasa R.. Chintala. Michael T.. Taylor. Joseph M.. Fox. Org. Synth.. 2014. 91. 322. 10.15227/orgsyn.091.0322.