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The Weinreb ketone synthesis or Weinreb–Nahm ketone synthesis is a chemical reaction used in organic chemistry to make carbon–carbon bonds. It was discovered in 1981 by Steven M. Weinreb and Steven Nahm as a method to synthesize ketones . [ 1 ]
The very facile reaction of Weinreb amides with organolithium and Grignard reagents results from the chelate stabilization in the tetrahedral adduct and, more importantly, the transition state leading to the adduct. The tetrahedral adducts are shown below. Weinreb ketone synthesis and tetrahedral intermediate stability
Other alternatives include forming a thioester or a Weinreb amide, then reducing the new species to an aldehyde through the Fukuyama reduction or Weinreb reaction respectively, or using catalytic hydrogenation as in the Rosenmund reaction. In the Weinreb ketone synthesis, an acyl chloride is first converted to the Weinreb amide, then treated ...
N,O-Dimethylhydroxylamine is a methylated hydroxylamine used to form so called 'Weinreb amides' for use in the Weinreb ketone synthesis. [2] It is commercially available as its hydrochloride salt. [1]
Steven M. Weinreb (born May 10, 1941) is an American chemist and is a professor of chemistry at Pennsylvania State University in United States. Together with Steven Nahm, he developed the Weinreb ketone synthesis, [1] which allows for mono-addition of an organometallic reagent such as a Grignard reagent or organolithium reagent to an amide.
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 ]
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. [1] [2] Dimethyl (diazomethyl)phosphonate 2 is often called the Seyferth–Gilbert reagent. [3] The Seyferth–Gilbert homologation
Addition of triethylamine to the activated alcohol leads to its oxidation to aldehyde or ketone and generation of dimethyl sulfide. In variance with other alcohol oxidation using "activated DMSO," the reactive oxidizing species is not generated by reaction of DMSO with an electrophile.