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The pinacol reaction is extremely well-studied and tolerates many different reductants, including electrochemical syntheses.Variants are known for homo- and cross-coupling, intra- and inter-molecular reactions with appropriate diastereo- or enantioselectivity; [2] as of 2006, the only unsettled frontier was enantioselective cross-coupling of aliphatic aldehydes. [3]
Akin to pinacol couplings, imines are susceptible to reductive coupling leading to 1,2-diamines. [40] Imine are oxidized with meta-chloroperoxybenzoic acid (mCPBA) to give an oxaziridines. Imines are intermediates in the alkylation of amines with formic acid in the Eschweiler-Clarke reaction.
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction.
A prominent early synthetic application of organoniobium chemistry was the use of dimethoxyethane niobium trichloride, NbCl 3 (DME), as a reagent for the reductive coupling of imines with carbonyl compounds to form amino alcohols. [9] This reagent has found further use in other pinacol-type reductive couplings. [10] [8]
Pinacol coupling and the corresponding diamine coupling [1] are possible in the presence of a one-electron reducing agent such as samarium(II) iodide. [ 1 ] Benzylic cations of chromium arene complexes are conformationally stable, and undergo only exo attack to afford S N 1 products stereospecifically, with retention of configuration. [ 1 ]
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The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material.
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