100-39-0Relevant articles and documents
Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid
Klein, Suzane M.,Zhang, Cungen,Jiang, Yu Lin
, p. 2638 - 2641 (2008)
A simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid (HI) is reported. The alkyl iodides were obtained in quick and easy work-up with good to excellent yields (66-94%) and very high purities (97-99%). Freshly prepared iodomethane and 1-iodobutane were applied to synthesize biologically relevant 3,7-dimethyladenine and 9-butyladenine, which were characterized thoroughly using 1D and 2D NMR, individually.
REACTIVITY OF t-BUTYLDIMETHYLSILYL ETHERS : A FACILE CONVERSION INTO BROMIDE
Mattes, Henri,Benezra, Claude
, p. 1697 - 1698 (1987)
TBDMS ether can be efficiently converted in one step into the corresponding bromides by a CBr4, PPh3 and acetone mixture.
Kinetics of the nucleophilic substitution of benzyltributylammonium bromide with allyl, butyl, and benzyl chlorides and with benzyl acetate and benzyl ether
Wang, Ten-Tsai,Chang, Chyi-Huang,Huang, Ting-Chia
, p. 615 - 626 (1996)
In this study, we investigated the kinetics of the nucleophilic substitutions, RX + (BzBu3NBr) ? RBr + (BzBu3NX), where R = allyl, Bu and Bz, when X = Cl; and X = AcO and BzO when R = Bz. The forward and backward rate constants in addition to the activation energies for R = allyl and Bu were also determined. However, only the rate constants at 35°C were determined for the benzyl compounds with toluene as the solvent to reduce the reaction rate. Moreover, the effects of the structures of the groups R and the leaving groups X on the reactivity were compared. Results in this study can provide valuable information for future studies involving the phase transfer catalyzed displacements.
Organic synthesis in water/carbon dioxide emulsions
Jacobson,Lee C.T.,DaRocha,Johnston
, p. 1207 - 1210 (1999)
The synthetic reaction between a hydrophobe, benzyl chloride, and a hydrophilic nucleophile, KBr, is reported in water-in-carbon dioxide (w/c) and carbon dioxide-in-water (c/w) emulsions. Emulsions containing equal amounts of water and CO2 were
Kinetics of the gas-phase elimination of α-bromophenylacetic acid under maximum inhibition
Chuchani, Gabriel,Dominguez, Rosa M.
, p. 725 - 728 (1999)
The gas phase elimination kinetics of the title compound was studied over the temperature range of 260.1-315.0 °C and pressure range of 20-70 Torr. This elimination, in seasoned static reaction system and in the presence of at least fourfold of the free r
Chlorotrimethylsilane/Lithium Bromide and Hexamethyldisilane/Pyridinium Bromide Perbromide: Effective and Selective Reagents for the Conversion of Alkyl (Cycloalkyl and Aralkyl) Alcohols into Bromides
Olah, George A.,Gupta, B. G. Balaram,Malhotra, Ripudaman,Narang, Subhash C.
, p. 1638 - 1639 (1980)
Alkyl bromides were obtained in high yield in the reaction of the corresponding alcohols with chlorotrimethylsilane/lithium bromide.The reaction was equally applicable to primary, secondary, and tertiary alcohols as well as to allylic and benzylic alcohols.High regioselectivity was observed in related conversions in which hexamethyldisilane/pyridinium bromide perbromide was used.Tertiary alcohols, for example, were converted selectively into the corresponding tertiary bromides in the presence of primary and secondary hydroxylic functions.The reactions were also highly steroselective.
STEREOSPECIFIC DISPLACEMENT OF SULFUR FROM CHIRAL CENTERS. ACTIVATION VIA THIAPHOSPHONIUM SALTS.
Krafft, Grant A.,Siddall, Thomas L.
, p. 4867 - 4870 (1985)
The first general method for direct displacement of sulfur from chiral carbon centers has been developed.Chiral mercaptans are readily converted to the corresponding thiaphosphonium salts by treatment with t-butyl hypochlorite and hexamethylphosphorous triamide.Metathesis with ammonium hexafluorophosphate provides stable, isolable, crystalline salts which undergo clean nucleophilic diplacement with a variety of heteroatom and carbon based nucleophiles, affording products in which the stereochemistry has been inverted.
Simple and rapid determination of the activation parameters of organic reactions by temperature-dependent NMR spectroscopy II. Application to reversible reactions
Satoh, Masahiro,Hirota, Minoru
, p. 2619 - 2624 (1996)
A non-isothermal (NIT) method for evaluating the activation enthalpies and entropies of reactions in solutions was applied to several reversible reactions. This was realized by a stepwise elevation of the temperature of a reaction system using a variable-temperature apparatus comprising on NMR spectrometer and a quick collection of FID (free induction decay) at every plateau of the step. The rate from NIT experiments agreed well with the previously measured rates by the conventional methods.
Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method
Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.
, p. 4176 - 4182 (2021)
Daptomycin (DAP) is a calcium (Ca2+)-dependent FDA-approved antibiotic drug for the treatment of Gram-positive infections. It possesses a complex pharmacophore hampering derivatization and/or synthesis of analogues. To mimic the Ca2+-binding effect, we used a chemoenzymatic approach to modify the tryptophan (Trp) residue of DAP and synthesize kinetically characterized and structurally elucidated regiospecific Trp-modified DAP analogues. We demonstrated that the modified DAPs are several times more active than the parent molecule against antibiotic-susceptible and antibiotic-resistant Gram-positive bacteria. Strikingly, and in contrast to the parent molecule, the DAP derivatives do not rely on calcium or any additional elements for activity.
Visible light induced 'on water' benzylic bromination with N-bromosuccinimide
Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej
, p. 1097 - 1099 (2006)
Benzylic bromination of various 4-substituted toluenes (Me, tert-Bu, COOEt and COMe) was effectively conducted with NBS in pure water and with a 40 W incandescent light-bulb as an initiator of the radical chain process, while electron donating groups (OMe and NHAc) directed the reaction to electrophilic aromatic substitution.
