16694-52-3Relevant articles and documents
ω-methylsulfanylalkyl glucosinolates: A general synthetic pathway
Mavratzotis, Manolis,Cassel, Stéphanie,Montaut, Sabine,Rollin, Patrick
, (2018/04/09)
A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-D-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds.
Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C-H Bonds with NaCl/Oxone at Room Temperature
Zhao, Mengdi,Lu, Wenjun
supporting information, p. 4560 - 4563 (2017/09/11)
A visible light-induced monochlorination of cyclohexane with sodium chloride (5:1) has been successfully accomplished to afford chlorocyclohexane in excellent yield by using Oxone as the oxidant in H2O/CF3CH2OH at room temperature. Other secondary and primary alkyl sp3 C-H bonds of cycloalkanes and functional branch/linear alkanes can also be chlorinated, respectively, under similar conditions. The selection of a suitable organic solvent is crucial in these efficient radical chlorinations of alkanes in two-phase solutions. It is studied further by the achievement of high chemoselectivity in the chlorination of the benzyl sp3 C-H bond or the aryl sp2 C-H bond of toluene.
Synthesis of a novel N-nitroalkyl bisindolylmaleimide
Roy, Sudipta,Gribble, Gordon W.
, p. 1879 - 1886 (2008/02/03)
We describe the synthesis of the novel N-nitropropyl bisindolylmaleimide 6. Copyright Taylor & Francis Group, LLC.
Glucosinolate chemistry. First synthesis of glucosinolates bearing an external thio-function
Mavratzotis,Dourtoglou,Lorin,Rollin
, p. 5699 - 5700 (2007/10/03)
A general strategy was developed to synthesize ω-methylthioalkyl glucosinolates through a coupling reaction between 1-thio-β-D-glucopyranose and a hydroximoyl halide obtained from the corresponding nitroalkyl methylsulfide precursor.
Structure, Synthesis, and Properties of Some Persubstituted 1,2-Dinitroethanes. In Quest of Nitrocyclopropyl-Anion Derivatives
Kai, Yasushi,Knochel,Paul,Kwiatkowski, Stefan,Dunitz, Jack D.,Oth, Jean F. M.,et al.
, p. 137 - 161 (2007/10/02)
Attempts to deprotonate nitrocyclopropane led to solutions which showed strong ESR. signals (Fig. 1) and from which 1-nitro-1'-nitroso-bicyclopropyl (3) and 1,1'-dinitro-bicyclopropyl (2) were isolated.The activation energy for rotation about the central C,C-bond of 2 is estimated to be about 12 kcal/mol (1H-NMR. spectra in Fig. 2).In contrast, the open-chain analoque 2,3-dimethyl-2,3-dinitrobutane (1) shows a metyl singlet down to -70 deg C.Low-temperature X-ray analyses of 1, 2, 3, and also of 1,1'-dinitro-bicyclobutyl (4) show that all four molecules have gauche-conformations but reveal striking structural differences between the open-chain and the cyclic derivatives (Fig. 4-6): the central C,C-bond is long in 1 (1.575 Angstroem), short in 2 (1.479 Angstroem); the C,N-bonds are long in 1 (1.549 Angstroem), short in 2 (1.488 Angstroem); the orientation of the nitro groups is bisected in 2 and perpendicular in 1.The crystal structure of the nitro-nitroso compound 3 is isimorphous with that of the dinitro compound 2 and thus disordered (Fig. 15-16).The effect of the nitro group as ?-electron acceptor on the molecular conformations and bond lengths is discussed.From analysis of the anisotropic vibrational parameters of 2 the root-mean-square librational amplitude of the nitro groups about their C,N-bonds is estimated to be about 5.8 deg at 95 K, corresponding to a rotational barrier of about 9 kcal/mol, i. e. the same order of magnitude as the NMR. estimate of about 12 kcal/mol for C,C-rotation.
