37857-25-3Relevant academic research and scientific papers
Gold(I)-catalyzed intramolecular hydroamination of N-allylic N′-arylureas to form imidazolidin-2-ones
Li, Hao,Song, Feijie,Widenhoefer, Ross A.
supporting information; experimental part, p. 955 - 962 (2011/06/25)
Treatment of N-allylic N′-arylureas with a catalytic 1:1 mixture of di-tert-butyl-o-biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol%) in chloroform at room temperature led to 5-exo-hydroamination to form the corresponding imidazolidin-2-ones in excellent yield. In the case of N-allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)-catalyzed 5-exo-hydroamination leads to formation of the corresponding trans-3,4-disubstituted imidazolidin-2-ones in excellent yield with ≥50:1 diastereoselectivity.
N-Allylhydroxylamines from 1,2-Addition of Allyl Grignard Reagents to Nitro Compounds: Generality and Drawbacks of the Reaction
Barboni, Luciano,Bartoli, Giuseppe,Marcantoni, Enrico,Petrini, Marino,Dalpozzo, Renato
, p. 2133 - 2138 (2007/10/02)
Allyl Grignard reagents react with both aromatic and aliphatic nitro derivatives via 1,2-addition to the nitro group.Conversely, nitroalkanes give either intractable mixtures or exclusively 1,4-conjugate addition.Nitroarenes with high steric hindrance at the ortho position and low aromatic stabilisation give competive or exclusive conjugate addition at the reactive para position.The 'in situ' treatment of the unstable 1,2-adducts with aluminium hydrides in the presence of catalytic amounts of palladium on charcoal provides a general method of synthesis ofN-allylhydroxylamines.LiAlH4 is a very efficient reducing agent, but, in some cases, it does not allow the reduction to be stopped at the hydroxylamino stage.Red-Al and DIBAL-H are less efficient but they ensure greater selectivity.Red-Al avoids the complete reduction to amines except when a strongly electron-donating substituent such as a methoxy group is present in the para position of the aromatic ring.Hydroxylamines can be obtained by reaction of nitrosoarenes followed by aqueous quenching.However, this alternative reaction does not offer any improvement, since relevant amounts of azo and azoxy derivatives are recovered as by-products.
TRANSFORMATION OF ALLYLSILANES INTO ALLYLAMINES VIA PHENYLTELLURINYLATION
Hu, Nan X.,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 4949 - 4952 (2007/10/02)
Allylsilanes were treated with benzenetellurinyl trifluoracetate below room temperature followed by amines at 65 deg.C in 1,2-dichloroethane in the presence of boron trifluoride etherate, readily giving allylamines.
