64342-39-8Relevant academic research and scientific papers
Copper Nitrate-Mediated Selective Difunctionalization of Alkenes: A Rapid Access to β-Bromonitrates
Gao, Mingchun,Zhou, Kaijing,Xu, Bin
supporting information, p. 2031 - 2036 (2019/03/28)
A regioselective copper nitrate-mediated difunctionalization of alkenes has been developed for the rapid synthesis of β-bromonitrates, where copper nitrate is used as an ideal nitrooxy source for the first time and the products will find many applications in organic synthesis as versatile synthons. Different from the general reports that copper nitrate acts as the nitro source, the given protocol provides a direct access to functionalized nitrates, with operational simplicity, good functional group tolerance and a wide substrate scope. (Figure presented.).
Can-mediated oxidative free radical reactions in an ionic liquid
Bar, Gregory,Bini, Fabien,Parsons, Andrew F.
, p. 213 - 222 (2007/10/03)
Cerium(IV) ammonium nitrate-mediated oxidative radical reactions are carried out in the presence of ionic liquids, including 1-butyl-3-methylimidazolium tetrafluoroborate, for the first time. The presence of the ionic liquid not only increases the rate and yield of reactions in dichloromethane but also extends the range of 1,3-dicarbonyl precursors, which can be utilized in these carbon-carbon bond-forming reactions.
An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide
Nair, Vijay,Panicker, Sreeletha B,Augustine, Anu,George, Tesmol G,Thomas, Siji,Vairamani
, p. 7417 - 7422 (2007/10/03)
Bromination of alkenes using a combination of potassium bromide and cerium(iv) ammonium nitrate (CAN) in a two phase system consisting of water and dichloromethane affords the corresponding dibromides in excellent yield. The reaction most likely involves the addition of the bromine radical generated from bromide ion by CAN and subsequent formation of the dibromide.
An 18O-Labeling Study of the β-(Nitroxy)alkyl and β-(Trifluoroacetoxy)alkyl Radical Migrations: Further Examples of a 1,2-Shift Mechanism
Crich, David,Filzen, G. Frederick
, p. 4834 - 4837 (2007/10/02)
The results of an 18O labeling study of the β-(nitroxy)alkyl and β-(trifluoroacetoxy)alkyl radical migrations are presented.Phenacyl bromide dimethyl acetal was hydrolyzed with H2(18)O water to give labelled phenacyl bromide and, following borohydride reduction, 18O labeled styrene bromohydrin.Nitration and trifluoroacetylation gave the radical precursors which were allowed to react with tributyltin hydride and AIBN in benzene at reflux.After cleavage to 2-phenylethanol, the rearrangement products were examined by GC-MS.The β-(nitroxy)alkyl migration is found to occur, in benzene to the extent of 64percent through a 1,2-, as opposed to a 2,3-shift, mechanism.The β-(trifluoroacetoxy)alkyl migration occurs 7percent by the 1,2-pathway.It is suggested that, in general, faster ester migrations occur to a greater extent through the 1,2-shift pathway.
BROMO- AND IODOFUNCTIONALIZATION OF OLEFINS BY MEANS OF THE MERCURY(II) SALT-HALOGEN COMBINATION
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 2416 - 2443 (2007/10/02)
Mercury(II) salts (fluoride, chloride, bromide, formate, acetate, trifluoroacetate, propionate, benzoate, nitrate, methanesulphonate, toluene-p-sulphonate, thiocyanate, and toluene-p-sulphinate) reacted with monoolefines and bromine or iodine to give 1,2-bifunctionalized products resulting from the addition of the halogen and the mercury(II) salt anion selectively.The addition was regiospecific for styrene and for 3,3-dimethylbut-1-ene affording Markownikoff type products, respectively.In the case of hex-1-ene both regioisomers were obtained.For cyclic alkenes trans-1,2-derivatives were stereoselectively obtained.Cycloocta-1,5-diene gave the monoaddition products.Buta-1,3-diene underwent mainly 1,2-addition and allylic derivatives gave the corresponding 1,2,3-trifunctionalized compounds.A possible ionic mechanism is proposed to explain the obtained addition products.
The Mercury(II) Salt-Halogen Combination HgX2-Hal2: A Versatile Reagent for Stereoselective Addition of Hal-X to Alkenes
Barluenga, Jose,Martinez-Gallo, Jose M.,Najera, Carmen,Yus, Miguel
, p. 1422 - 1423 (2007/10/02)
The reaction of mercury(II) salts (fluoride, chloride, bromide, nitrate, methanesulphonate, toluene-p-sulphinate, and toluene-p-sulphonate) and halogens (bromine or iodine) with alkenes leads to the corresponding 1,2-bifunctionalized products resulting fr
