Despite of very small side differentiation in 3-Li the ratio of cis-3: trans-3 can be shifted from 41: 59 to 85: 15 by variation of the proton sources.
OXIDATIVE CONVERSION OF ALIPHATIC ALDEHYDES TO NITRILES USING OXOAMMONIUM SALT
The present invention relates to an oxidative transformation method of aliphatic benzaldehydes to nitriles using NH_4OAc through oxoammonium salts. By using stoichiometric amounts of oxoammonium salts to establish optimal reaction conditions associated with the oxidative conversion of aliphatic benzaldehydes to nitriles, high yields of nitrile can be selectively obtained, and the oxoammonium salts used can be oxidized and reused in a simple method.COPYRIGHT KIPO 2020
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Paragraph 0055-0063; 0136-0142
(2019/12/10)
Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate
An efficient and scalable route for the synthesis of nitriles was developed by oxoammonium salt (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) mediated oxidative conversion of aldehydes with NH4OAc. A variety of aliphatic aldehydes as well as benzaldehydes were converted into the corresponding nitriles in high yields. The nitroxyl radical which is the reduced species of the used oxoammonium salt was recovered by simple acid-base extraction for the recycling.
Kim, Myeong Jin,Mun, Junyoung,Kim, Jinho
supporting information
p. 4695 - 4698
(2017/11/17)
Stereoselective Protonation of Carbanions, 1. - Diastereoselective Protonation of C-H-Activated Cyclohexane Derivatives
The diastereoselectivity of the kinetically controlled protonation of carbanions derived from 4-tert-butyl-1-X-cyclohexanes (1: X = CN, 2: X = CO2Me, 2-Si: X = C(OMe)OSiMe3, 3: X = COPh, 4: X = SO2Ph) is systematically investigated.By variation of (a) the
Electrochemical oxidation of ketone acylhydrazones and their HCN adducts in NaCN-MeOH. Tranformation of ketones to nitriles
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Okimoto,Chiba
p. 1070 - 1076
(2007/10/02)
The Stereochemistry of Organometallic Compounds. XXII The Stereochemistry of Metal-Catalysed Hydrogen Cyanide Addition to Olefins
Reactions of (E)-3,3-dimethyl(1,2-D2)but-1-ene with hydrogen cyanide and of (E)-3,3-dimethyl(1-D)but-1-ene with deuterium cyanide have been shown to proceed in a completely stereospecific cis fashion when a catalyst system based on Pd(diop)2 was used.Reaction between 4-t-butylcyclohexene and deuterium cyanide with the catalyst system gave only the equatorial nitriles trans-4-t-butylcyclohexane-1-carbonitrile and cis-3-t-butylcyclohexane-1-carbonitrile with cis incorporation of deuterium.Use of a catalyst system based on Ni4 and zinc chloride led to significant amounts of isotopic exchange and rearrangement.These results are compared with those from hydroformylation of the olefins, and the mechanism of hydrocyanation is discussed
Jackson, W. Roy,Lovel, Craig G.
p. 2053 - 2067
(2007/10/02)
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