109-65-9Relevant articles and documents
Mild conversion of alcohols to alkyl halides using halide-based ionic liquids at room temperature
Ren, Rex X.,Wu, Jeff Xin
, p. 3727 - 3728 (2001)
Formula presented Alcohols were efficiently converted to alkyl halides using 1-n-butyl-3-methylylimidazolium halides (ionic liquids) in the presence of Bronsted acids at room temperature. The alkyl halide products were easily isolated from the reaction mixture via simple decantation or extraction, and the 1-n-butyl-3-methylimidazolium cation could be recycled for further uses.
Convergent synthesis of a deuterium-labeled serine dipeptide lipid for analysis of biological samples
Dietz, Christopher,Clark, Robert B.,Nichols, Frank C.,Smith, Michael B.
, p. 274 - 285 (2017)
Bacterial serine dipeptide lipids are known to promote inflammatory processes and are detected in human tissues associated with periodontal disease or atherosclerosis. Accurate quantification of bacterial serine lipid, specifically lipid 654 [((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-l-serine, (3S)-l-serine] isolated from Porphyromonas gingivalis, in biological samples requires the preparation of a stable isotope internal standard for sample supplementation and subsequent mass spectrometric analysis. This report describes the convergent synthesis of a deuterium-substituted serine dipeptide lipid, which is an isotopically labeled homologue that represents a dominant form of serine dipeptide lipid recovered in bacteria.
STABILIZATION IN THE ORDER I>Br>Cl AMONG TRIMETHYLSILYLMETHYL HALIDES, COMPARED TO CARBON ANALOGS. POSSIBLE ROLE OF ELECTRONEGATIVITY IN ORGANOSILICON CHEMISTRY
Peterson, Paul E.
, p. 1295 - 1298 (1981)
Electronegativities may be used to rationalize the observation that the equilibrium, CH3(CH2)3I + (CH3)3SiCH2Cl CH3(CH2)3Cl + (CH3)3SiCH2I, lies to the right.
Tributylarsonium-2,2,3,3,4,4-hexafluorocyclobutane Ylide. Preparation and Cleavage
Burton, Donald J.,Valk, Paul D. Vander
, p. 413 - 416 (1981)
F-cyclobutane forms a stable ylide with n-tributylarsine.In contrast to the halogen cleavage of the analogous phophonium ylide, which gives 1,1-dihaloalkanes, the arsonium ylide reacts with bromine and iodine to give the 1-halo-F-cyclobutenes.
A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010
Cai, Dongwei,Hughes, David L.,Verhoeven, Thomas R.
, p. 2537 - 2540 (1996)
Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-bromo-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield.
1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine
Buonomo, Joseph A.,Cole, Malcolm S.,Eiden, Carter G.,Aldrich, Courtney C.
, p. 3583 - 3594 (2020/09/15)
The recently reported chemoselective reduction of phosphine oxides with 1,3-diphenyldisiloxane (DPDS) has opened up the possibility of additive-free phosphine oxide reductions in catalytic systems. Herein we disclose the use of this new reducing agent as an enabler of phosphorus redox recycling in Wittig, Staudinger, and alcohol substitution reactions. DPDS was successfully utilized in ambient-temperature additive-free redox recycling variants of the Wittig olefination, Appel halogenation, and Staudinger reduction. Triphenylphosphine-promoted catalytic recycling reactions were also facilitated by DPDS. Additive-free triphenylphosphine-promoted catalytic Staudinger reductions could even be performed at ambient temperature due to the rapid nature of phosphinimine reduction, for which we characterized kinetic and thermodynamic parameters. These results demonstrate the utility of DPDS as an excellent reducing agent for the development of phosphorus redox recycling reactions.
Method of preparing 1-bromobutane continuously
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Paragraph 0037-0064, (2018/12/14)
The invention discloses a method of preparing 1-bromobutane continuously. 1-bromobutane is produced continuously by carrying out a reaction within a short time in a micro reactor without a catalyst bytaking normal butanol and hydrobromic acid as raw materials. Two strands of materials enter the micro reactor through a metering pump and are preheated, mixed and reacted to obtain a coarse product 1-bromobutane. Compared with the prior art, a catalyst sulfuric acid is not used, so that treatment of sulfuric acid at the back end is reduced, the separation process is simplified, the environmentalpollution is reduced, the utilization ratio of hydrobromic acid is high, the conversion rate of reactants is high, and the selectivity and yield of a target product are relatively high and the like. The method is simple and safe to operate, can be used for producing 1-bromobutane continuously with a high yield, and has a good industrial application prospect.
An efficient conversion of alcohols to alkyl bromides using pyridinium based ionic liquids: A green alternative to appel reaction
Das, Pranab J.,Das, Jupitara,Das, Dimpee
, p. 651 - 654 (2018/02/09)
Pyridinium based ionic liquids namely 4-alkylpyridinium bromides were prepared and used for the conversion of alcohols to alkyl bromides in the presence of p-toluenesulphonic acid in the absence of volatile organic compounds. This solvent free procedure promises to be a much improved and environmentally benign alternative to the Appel reaction.
Why is cis/trans stereoinversion with Li+(THF)4 migration across the phenyl ring of α-lithiostyrene accelerated by two ortho-methyl groups?
Knorr, Rudolf,Lattke, Ernst,Ruhdorfer, Jakob,Ferchland, Kathrin,von Roman, Ulrich
, p. 1621 - 1631 (2018/02/28)
Common wisdom might anticipate that two methyl groups placed on a molecular migration route should act as an impediment. However, the “conducted tour” migration of Li+(THF)4 across the aryl ring (“π-route”) during the cis/trans stereoinversion of α-arylvinyllithiums had been found to occur with practically equal velocities in the presence of either one or two ortho-alkyl substituents. We now report that the omission of both ortho-methyl groups retards the stereoinversion process. In order to arrive at an answer to the title question, we investigate the aggregation equilibria and microsolvation states of ortho, ortho′-unsubstituted α-lithiostyrenes by means of approved secondary NMR criteria. Beyond such necessary knowledge about the ground-state properties, we provide kinetic evidence showing that the retarded cis/trans stereoinversion of α-lithiostyrene proceeds by the pseudomonomolecular, ionic mechanism with Li+(THF)4 migration.
Facile continuous process for gas phase halogen exchange over supported alkyl phosphonium salts
Sharma, Priti,Sasson, Yoel
, p. 2824 - 2828 (2018/02/06)
Chloride-bromide halogen exchange was realized when a mixture of an alkyl chloride and an alkyl bromide were reacted over a supported molten alkyl phosphonium catalyst. Conversion was found to be near equilibrium in a tubular flow reactor at 150 °C and 1500 GHSV. The catalyst was prepared by impregnation of alumina or silica support and found to be highly stable for relatively long periods of time. A pathway for the catalytic cycle is proposed.
