28437-97-0

Upstream product

• 26385-08-0 N-(2-chloro-1-phenylethyl)acetamide 
• 100-42-5 styrene 
• 75-05-8 acetonitrile 
• 78837-69-1 N-[1-phenyl-2-(phenylselanyl)ethyl]acetamide 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 96-09-3 styrene oxide 
• 13684-98-5 2-methoxy-2-phenylethyl iodide 

Downstream Products

• 24666-05-5 2-(N-acetylamino)-2-phenylethanol 
• 496927-30-1 3-phenyl-2,3-dihydrooxazolo[3,2-c]pyrimidine-5,7-(6H)-dione 

Relevant academic research and scientific papers

REGIOSPECIFIC PREPARATION OF 2-OXAZOLINES PROMOTED BY SILICON TETRAFLUORIDE

Silicon tetrafluoride promotes reaction of oxiranes with nitriles to give 2-oxazolines in good yield.

One-pot conversion of alkenes into oxazolines and oxazolidin-2-ones promoted by diphenyl diselenide

Oxazolines or oxazolidin-Zones are produced from the reaction of diphenyl diselenide, ammonium persulfate and trifluoromethanesulfonic acid with alkenes in the presence of MeCN/H2O, NH2CN/H2O or NH2CO2Et.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

Various alkenes (internal, terminal, aryl and alkyl substituted) and 1,2-diphenylethyne were efficiently and selectively dibrominated using 2 equivalents of 48% aqueous hydrobromic acid, with air as an oxidant and sodium nitrite as a catalyst. Despite the presence of water, only trans dibromination occurred producing anti-1,2-dibromoalkanes and (E)-1,2-dibromo-1,2- diphenylethene. A comparison of resource demand, waste production and environmental, health and safety issues of the NaNO2 catalyzed aerobic bromination with molecular bromine and other oxidative bromination methods revealed that the proposed method is not only selective and effective but has a better environmental profile.

Stereoselective one-pot synthesis of oxazolines

(Chemical Equation Presented) Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)2 or Zn(OTf)2 is reported to furnish oxazolines in one pot and good yields. The reaction is equally applica

Intramolecular nucleophilic deselenenylation reactions promoted by benzeneselenenyl triflate. Stereospecific synthesis of vicinal amino alcohol precursors

After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides, containing internal oxygen or nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and oxazolidin-2-ones has been developed.

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.

A CONVENIENT SYNTHETIC METHOD OF 1,3-DISUBSTITUTED ISOQUINOLINES USING SILVER TRIFLUOROMETHANESULFONATE AS A KEY REAGENT

1,3-Disubstituted isoquinolines were prepared under mild conditions from allylbenzenes and nitriles using silver trifluoromethanesulfonate and iodine.