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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.
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 ...
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–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 ]
As such they are used in cyclopropanation for example in the reaction of ethyl diazoacetate with styrene. [22] Certain diazo compounds can couple to form alkenes in a formal carbene dimerization reaction. Diazo compounds are intermediates in the Bamford–Stevens reaction of tosylhydrazones to alkenes, again with a carbene intermediate:
The Diels-Alder reaction is perhaps the most important and commonly taught cycloaddition reaction. Formally it is a [4+2] cycloaddition reaction and exists in a huge range of forms, including the inverse electron-demand Diels–Alder reaction, hexadehydro Diels–Alder reaction and the related alkyne trimerisation.
Ethyl and benzyl esters are easily made thereby, and the reaction is noteworthy in that even the highly hindered tert-butyl alcohol gives very high yields in this synthesis. [ 8 ] Levi and Zanetti extended the Knorr synthesis in 1894 to the use of acetylacetone (2,4-pentanedione) in reaction with ethyl 2-oximinoacetoacetate.
The Kulinkovich reaction form cyclopropanols via a reaction between esters and Grignard reagents in presence of a titanium alkoxide. The Bingel reaction is a specialised cyclopropanation reaction used to functionalise a fullerene. In the di-π-methane rearrangement, photochemical stimulation causes 1,4-dienes to rearrange to form ...