Methyl phenyldiazoacetate

Methyl phenyldiazoacetate is the organic compound with the formula C6H5C(N2)CO2Me.

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.

Solid state structure of t -BuO 2 CC(N 2 )C 6 H 4 NO 2 , a representative donor-acceptor carbene related to the title compound. Key distances: C-N = 1.329 Å, N-N = 1.121 Å. [ 4 ]