Methyl phenyldiazoacetate is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula C
6H
5C(N
2)CO
2Me. It is a
diazo derivative of
methyl phenylacetate
Methyl phenylacetate is an organic compound that is the methyl ester of phenylacetic acid, with the structural formula C6H5CH2COOCH3. It is a colorless liquid that is only slightly soluble in water, but soluble in most organic solvents.
Methyl ...
. 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
Rhodium(II) acetate is the coordination compound with the formula Rh2(AcO)4, where AcO− is the acetate ion (). This dark green powder is slightly soluble in polar solvents, including water. It is used as a catalyst for cyclopropanation of a ...
or related chiral complexes. Methyl phenyldiazoacetate is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base.
References
{{Reflist
Diazo compounds
Reagents for organic chemistry