2-methyl-2-butyl fluoride

Halo-2-methylbutanes (X = F, Cl, Br) all produce the same carbocation upon dissociation, yet one of these halides is unreactive. Calculate the dissociation energies for 2-methyl-2-butyl fluoride and 2-methyl-2-butyl-chloride. (Energies of fluoride and chloride are given at right.) Compare these to the dissociation energy of the corresponding bromo derivative. Which halide is most likely to be unreactive ... 

Alkyl fluoride boron trifluoride systems were first investigated by Olah et al. (1957). 1 1 Addition complexes were observed at low temperatures, and their specific conductivity was measured. The specific conductivity of the propyl and butyl fluoride boron trifluoride systems was found three orders of magnitude larger than those of the methyl- and ethyl-fluoride systems. The latter systems on heating dissociated into their starting materials, whereas the former gave polymer mixtures (Olah, unpublished). 

The. S n reactions between HF and protonated methyl, ethyl, isopropyl, and /-butyl fluorides in the gas phase have been examined at the MP2/6-31+- -G(d,p) level of theory.112 113 The reaction of CH3FH+ clearly occurs via back-side attack as the transition state for this process is of lower energy than the transition state for frontside attack. The EtFH+ can react via a more stable back-side. S N2 reaction or an. S n 1 reaction via front-side attack since the. S N 1 pathway is 4.4 kJmol-1 lower in energy. No. S n2 path could be found for i-PrFH+ and the front- and back-side pathways had equal activation energies for /-BuFH+, which effectively reacts by an. S N1 mechanism. The conclusion is that the preference for back-side attack is reduced as the size of... 

Other Organic Compounds aniline hydrochloride benzyl hydroperoxide butyl chloride dicyclohexyl peroxide diethyl sulfide methyl iodide 2-naphthoyl bromide sodium S-phenyl thiosulfite fert-butyl fluoride... 

Aniline hydrochloride Benzyl hydroperoxide Butyl chloride Dicyclohexyl peroxide Diethyl sulfide Methyl iodide 2-Naphthoyl bromide Sodium S-phenyl thiosulfite ferf-Butyl fluoride... 

Aniline Elydrochloride Benzyl Elydroperoxide Butyl Chloride Dicyclohexyl Peroxide Diethyl Sulfide Methyl Iodide 2-Naphthoyl Bromide Sodium S-Phenyl Thiosulfite ferf-Butyl Fluoride... 

In t-butyl fluoride, there exists only one species of hydrogen which is the hydrogen of the methyl groups. 

CALCULATION OF THE THERMODYNAMIC FUNCTIONS OF T-BUTYL FLUORIDE /2-FLUORO-2-METHYL PROPANE/. 

CALCULATION OF THE THERMODYNAMIC FUNCTIONS OF T-BUTYL FLUORIDE /2-FLUORO-2-METHYL PROPANE/. //ENGLISH TRANSLATION OF ZH. FIZ. KHIM. 42 /12/ 3043-. 1968.//... 

Copolymers from tetrafluoroethylene and 40% perfluorovinyl methyl ether are also elastomers (glass-transition temperature — 12°C). The copolymerization is carried out in aqueous emulsion with ammonium perfluoro-octanoate as emulsifier. Vulcanization is possible with hexamethylene diamine via the small amount of perfluoro(4-carboxy methyl butyl vinyl ether) also polymerized into the copolymer. This ether is produced from perfluoroglutaryl fluoride and hexafluoropropylene oxide. 

Wiberg and Zilm used the Atoms in Molecules based IGAIM method to calculate the F NMR shielding for the alkyl fluorides from methyl fluoride to i-butyl fluoride and to separate it into the contribution from each of the MOs. 

Both methyltriethylphosphonium fluoride and methyltributylphospho-nium fluoride have been prepared The latter generates benzyl fluoride from benzyl chloride in 80% yield and ethyl fluoroacetate from ethyl bromoacetate in 53% yield Methyltnbutylphosphonium fluoride converts 1-bromododecane to a 50 50 mixture of 1-fluorododecane and 1-dodecene Methyltnbutylphosphonium fluoride also quantitatively forms styrene from 1-bromo-1-phenylethane [26] Methyl-tnbutylphosphonium fluonde is the reagent of choice for the conversion of N,N dimethylchloroacetamide to its fluoride, but it is not able to convert chloro-acetonitnle to fluoroacetomtrile Methyltnbutylphosphonium fluoride changes chloromethyl octyl ether to the crude fluoromethyl ether in 66% yield The stereoselectivity of methyltnbutylphosphonium fluoride is illustrated by the reac tions of the 2-tert-butyl-3-chlorooxiranes [27] (Table 2)... 

Neither methyl nor ethyl fluoride gave the corresponding cations when treated with SbFs. At low temperatures, methyl fluoride gave chiefly the methylated sulfur dioxide salt, (CH3OSO) ShF while ethyl fluoride rapidly formed the rert-butyl and ferf-hexyl cations by addition of the initially formed ethyl cation to ethylene molecules also formed ° At room temperature, methyl fluoride also gave the tert-butyl cation. In accord with the stability order, hydride ion is abstracted from alkanes by super acid most readily from tertiary and least readily from primary positions. 

KHC03, NaOAc, K2HP04, Na3P04, triethyl amine) and finally sodium carbonate was selected as the base of choice. Fluoride initiated Suzuki coupling with KF was unsuccessful. Dimethoxy ether was selected as the solvent after screening a variety of solvents (acetone, tetrahydrofuran, methanol, isopropyl alcohol, and methyl-i-butyl ether). 

When sodium ethoxide is used in place of sodium hydroxide in the carbonylation reaction of benzyl halides with dicobalt octacarbonyl, ethyl esters are produced instead of the acids [15], Esters are also produced directly from iodoalkanes through their reaction with molybdenum hexacarbonyl in the presence of tetra-/i-butylammo-nium fluoride [16]. Di-iodoalkanes produce lactones [16]. The reaction can be made catalytic in the hexacarbonyl by the addition of methyl formate [16]. t-Butyl arylacetic esters are produced in moderate yield (40-60%) under phase-transfer catalytic conditions in the palladium promoted carbonylation reaction with benzyl chlorides [17]. 

E-2-bromomethyleneglutaric esters (>70%) have been obtained from the corresponding 2-bromo-2-bromomethylglutarates using a 25% excess tetra-n-butyl-ammonium fluoride in HMPA [24], A similar procedure converts dimethyl 2-bromo-2-bromomethylsuccinate into dimethyl Z-2-bromomethylenefumarate [25], whereas methyl 2,2-bis(bromomethyl)ethanoate yields the 2-bromomethyl-propenoate when reacted with aqueous sodium hydroxide in the presence of benzyl-triethylammonium chloride [26]. No hydrolysis of the ester is evident at 0°C, but becomes apparent at 25 °C. 

Nakane ei al. (1964) established equilibrium constants of boron isotope exchange between boron trifluoride gas on one side and boron trifluoride methyl fluoride, methyl chloride, isopropyl chloride and t-butyl chloride. The value of the equilibrium constants, which represents the thermodynamic isotope effect, was related to the polarity, stability and catalytic activity of the complexes. 

Ethyl fluoride shows more tendency to ionize in antimony pentafluoride, than does methyl fluoride. The solutions in neat antimony pentafluoride are, however, not stable and a rapid formation of t-butyl and t-hexyl cations is observed. This observation indicates self alkylation of ethylene formed in equilibrium of equation (2). 

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