2316-64-5Relevant articles and documents
A Quantitative Assay of Sodium Triacetoxyborohydride
Zacuto, Michael J.,Perona, Joseph,Dunn, Robert
, p. 2080 - 2087 (2019)
Sodium triacetoxyborohydride (STAB) is a common reducing agent with potency that degrades over time and is not uniformly assigned. A simple assay based on an aldehyde reduction has been developed to determine the active borohydride content of this reagent. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against the H2 evolution method as well as yields obtained from a reductive amination. The use of these assay data to adjust the STAB charge as well to optimize a reductive amination has been demonstrated.
Synthesis, characterization and Twin Polymerization of a novel dioxagermine
Kitschke, Philipp,Auer, Alexander A.,Seifert, Andreas,Rüffer, Tobias,Lang, Heinrich,Mehring, Michael
, p. 472 - 478 (2014)
The synthesis of 6-bromo-2,2-di-tert-butyl-4H-1,3,2-benzo[d]dioxagermine (1) via an alcohol/alkoxide exchange starting from di-tert-butyl-di-ethoxy germane is reported. Characterization of the title compound including single crystal X-ray diffraction and TGA/DSC analysis, mass spectrometry, 1H NMR, 13C{1H} NMR and IR spectroscopy is reported. DFT-D calculations have been carried out to assign the absorption band maxima of the IR spectrum to the corresponding vibrational modes. The suitability for Twin Polymerization of the novel dioxagermine 1 has been studied by TGA/DSC analysis and mass spectrometry. Proton-assisted Twin Polymerization of 1 results in an organic-inorganic hybrid material composed of a phenolic resin and [ tBu2GeO]n.
Diels-Alder reaction of 4-bromo-6-spiroepoxycyclohexa-2,4-dienone with electron-rich and neutral dienophiles
Bonnarme, Vincent,Bachmann, Christian,Cousson, Alain,Mondon, Martine,Gesson, Jean-Pierre
, p. 433 - 448 (1999)
Spirodienone 1, prepared by Adler-Becker oxidation of 4-bromo-2- hydroxymethylphenol, undergoes [4+2] cycloaddition with various dienophiles (enol ethers, enol esters, styrenes, N-methylvinylacetamide) under thermal conditions (20-160°C). Three sets of experiments have been carried out, either with CH2Cl2 as solvent or neat with 1, or under tandem oxidation- cycloaddition conditions with phase-transfer catalysis. Complete regio- and syn diastereofacial selectivities were obtained but a switch in endo/exo selectivity has been observed between enol ethers and styrenes (endo addition), enol esters (low selectivity) and an enamide (exo addition). The FMO analysis confirms that theses reactions are under LUMO(diene) control and that the observed regioselectivity is in agreement with orbital coefficients. Except for vinyl acetate, the formation of the major isomer is qualitatively confirmed at the AM1 level.
Enthalpies, Free Energies, and Entropies of Transfer of Phenols from Nonpolar Solvents to Water
Haberfield, Paul,Kivuls, Juris,Haddad, Michael,Rizzo, Thomas
, p. 1913 - 1916 (1984)
The enthalpies of transfer of seven phenols from 1-octanol to water and from toluene to water were determined by calorimetry.In the case of two phenols, whose rate of solution in water was found to be too slow for measurement by the usual heat of solution method, a new two-phase titration method was employed.The free energies of transfer between these solvents were determined by measuring the appropriate partition coefficients.The nature of the nonpolar solvent (toluene or 1-octanol) was found to cause large changes in the average values of the thermodynamic parameters of transfer into water, as well as changes in the ordering of the phenols in the series with respect to these transfer parameters.A curious correlation was observed between the octanol-water partition coefficients and the toluene -> water entropies of transfer.
A synthetic approach to chrysophaentin F
Vendeville, Jean-Baptiste,Matters, Rebecca F.,Chen, Anqi,Light, Mark E.,Tizzard, Graham J.,Chai, Christina L. L.,Harrowven, David C.
supporting information, p. 4837 - 4840 (2019/05/02)
The chrysophaentins are a newly discovered natural product family displaying promising anti-infective activity. Herein we describe an approach to chrysophaentin F that uses an array of metal catalysed coupling reactions (Cu, Ni, Pd, W, Mo) to form key bonds.
