84388-60-3

Upstream product

• 530-36-9 2-amino-1,2-diphenylethanol 
• 108-24-7 acetic anhydride 
• 64-17-5 ethanol 
• 7726-95-6 bromine 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 75-36-5 acetyl chloride 
• 574-15-2 (E)-benzil monooxime 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 70369-11-8 trans-4,5-diphenyl-2-methyl-Δ²-oxazoline 
• 141-78-6 ethyl acetate 
• 100-52-7 benzaldehyde 
• 100422-87-5 (α-acetamidobenzyl)trimethylsilane 
• 100422-85-3 (α-phthalimidobenzyl)trimethylsilane 

Downstream Products

• 3893-31-0 N-(2-oxo-1,2-diphenylethyl)acetamide 
• 1721-96-6 1-methyl-3-phenylisoquinoline 
• 195625-00-4 N-(L(g)-threo-α'-hydroxy-bibenzyl-α-yl)-acetamid; N-acetyl-(-)-isodiphenylhydroxyethylamine 
• 195625-08-2 threo-2-Acetamino-1.2-diphenyl-aethan-1-ol 
• 101023-17-0 threo-2-acetamido-1,2-diphenylethyl acetate 
• 1721-82-0 1-methyl-4-phenylisoquinoline 
• 94675-09-9 (+/-)-N-(erythro-α'-methoxy-bibenzyl-α-yl)-acetamide 

Relevant academic research and scientific papers

Bromination of Alkenes in Acetonitrile. A Rate and Product Study

The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols.These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts.These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes.The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3(1-) with the alkene.The incorporation of MeCN was Markovnikov and stereospecifically anti.The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations.A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.

Nucleophilic Aminomethylation of Aldehydes with α-Amino Alkylsilanes

Fluoride-induced desilylation of (α-phthalimido-, α-morpholino-, and α-acetamidobenzyl)silanes and a (phthalimidomethyl)silane generates the corresponding α-amino carbanions which add to a variety of aldehydes.The conversion of phthalimido group of the adducts into amino moiety leads to β-amino alcohols.This simple reaction sequence offers a new and general method of nucleophilic aminomethylation.