497-36-9Relevant articles and documents
A solution of borane in tetrahydrofuran. A stereoselective reducing agent for reduction of cyclic ketones to thermodynamically more stable alcohols
Cha,Moon,Park
, p. 7514 - 7515 (2001)
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276. Hydroboration and Oxymercuration of Some 1-Substituted Norborn-2-enes
Luef, Wolfgang,Voegeli, Ulrich-Christian,Keese, Reinhart
, p. 2729 - 2739 (1983)
The 1-substituted norborn-2-enes 11-13 and 18 react with electrophiles under kinetic control preferentially in 2-position.The regioselectivity in oxymercuration is higher than in hydroboration and reaction with aqueous palladium chloride.
Decomposition of endo- and exo-(2-Norbornyl)formyl m-Chlorobenzoyl Peroxides
Walling, Cheves,Humphreys, Robert R. W.,Sloan, John P.,Miller, Traci
, p. 5261 - 5263 (1981)
The subject peroxides undergo first-order decomposition in several solvents with rates increasing moderately with solvent polarity and endo/exo rates in a ratio of 1:10-100.Carboxyl inversion product, ROCOOCOAr, and other "polar" products are formed with no evidence for significant free-radical production.Products from an exo-peroxide have exclusively exo configurations, but carboxyl inversion product from endo peroxide contains small amounts of exo isomer.In acetic acid, 2-norbornyl acetate is a major product, with endo/exo ratio of 14:86 from the endo-peroxide.Optically active exo-peroxide in acetic acid gives exo-2-norbornyl acetate with 6percent net retention of configuration.The results are discussed in terms of successive ion pairs and carboxyl inversion product arising early on the reaction path and other products later.
Liquid-phase oxidation of olefins with rare hydronium ion salt of dinuclear dioxido-vanadium(V) complexes and comparative catalytic studies with analogous copper complexes
Maurya, Abhishek,Haldar, Chanchal
, (2021/02/26)
Homogeneous liquid-phase oxidation of a number of aromatic and aliphatic olefins was examined using dinuclear anionic vanadium dioxido complexes [(VO2)2(salLH)]? (1) and [(VO2)2(NsalLH)]? (2) and dinuclear copper complexes [(CuCl)2(salLH)]? (3) and [(CuCl)2(NsalLH)]? (4) (reaction of carbohydrazide with salicylaldehyde and 4-diethylamino salicylaldehyde afforded Schiff-base ligands [salLH4] and [NsalLH4], respectively). Anionic vanadium and copper complexes 1, 2, 3, and 4 were isolated in the form of their hydronium ion salt, which is rare. The molecular structure of the hydronium ion salt of anionic dinuclear vanadium dioxido complex [(VO2)2(salLH)]? (1) was established through single-crystal X-ray analysis. The chemical and structural properties were studied using Fourier transform infrared (FT-IR), ultraviolet–visible (UV–Vis), 1H and 13C nuclear magnetic resonance (NMR), electrospray ionization mass spectrometry (ESI-MS), electron paramagnetic resonance (EPR) spectroscopy, and thermogravimetric analysis (TGA). In the presence of hydrogen peroxide, both dinuclear vanadium dioxido complexes were applied for the oxidation of a series of aromatic and aliphatic alkenes. High catalytic activity and efficiency were achieved using catalysts 1 and 2 in the oxidation of olefins. Alkenes with electron-donating groups make the oxidation processes easy. Thus, in general, aromatic olefins show better substrate conversion in comparison to the aliphatic olefins. Under optimized reaction conditions, both copper catalysts 3 and 4 fail to compete with the activity shown by their vanadium counterparts. Irrespective of olefins, metal (vanadium or copper) complexes of the ligand [salLH4] (I) show better substrate conversion(%) compared with the metal complexes of the ligand [NsalLH4] (II).
Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie
supporting information, p. 4119 - 4129 (2020/08/10)
A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).
