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Ethyl diazoacetate (N=N=CHC(O)OC 2 H 5) is a diazo compound and a reagent in organic chemistry. It was discovered by Theodor Curtius in 1883. [4] The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water. As a carbene precursor, it is used in the cyclopropanation of alkenes.
In organic chemistry, the Roskamp reaction is a name reaction describing the reaction between α-diazoesters (such as ethyl diazoacetate) and aldehydes to form β-ketoesters, often utilizing various Lewis acids (such as BF 3, SnCl 2, and GeCl 2) as catalysts. [1] [2] [3] The reaction is notable for its mild reaction conditions and selectivity.
The Buchner ring expansion is a two-step organic C-C bond forming reaction used to access 7-membered rings. The first step involves formation of a carbene from ethyl diazoacetate, which cyclopropanates an aromatic ring. The ring expansion occurs in the second step, with an electrocyclic reaction opening the cyclopropane ring to form the 7 ...
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]
This reaction is also called the Regitz diazo transfer. [7] Examples are the synthesis of tert-butyl diazoacetate [8] and diazomalonate. [9] Methyl phenyldiazoacetate is generated in this way by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. [10] [11]
The reaction of quadricyclane with DEAD is a 2σ + 2σ + 2π cycloaddition that on water takes place within 10 minutes at room temperature with 82% yield. The same reaction in toluene takes 24 hours at 80 °C with 70% yield. An emulsion reaction in fluorinated cyclohexane takes 36 hours and the neat reaction takes even longer (48 hours).
A diazo cross-coupling reaction has also been reported between ethyl diazoacetate and methyl phenyldiazoacetate using the rhodium catalyst [Rh 2 (OPiv) 4]. [ 5 ] A direct metal carbene dimerization has been used in the synthesis of novel Polyalkynylethenes [ 6 ]
Cascade reactions are often key steps in the efficient total synthesis of complex natural products. The key step in Heathcock's synthesis of dihydroprotodaphniphylline features a highly efficient cascade involving two aldehyde/amine condensations, a Prins-like cyclization, and a 1,5-hydride transfer to afford a pentacyclic structure from an acyclic starting material.