Alkyl octyl iodide

The critical advantage of the quaternary phosphonium iodides is their excellent temperature stability. For example, the selected tetra(alkyl)phosphonium iodide salt, tri(n-octyl)(n-octadecyl) phosphonium iodide [(n-Oct)3(n-Octadecyl)P i, referred to as TOP18 ], shows no TGA weight loss up to 300°C. 

This loss of catalyst and contamination of product with benzene caused us to select the more stable tri(n-alkyl)tin iodides. These catalysts are not as active as the triaiyltin iodides but exhibit veiy good stability under normal reaction conditions. They are also readily prepared from industrially-available bulk starting materials. Tri(n-octyl)tin iodide [(n-Oc sSnl, referred to as "TOT"] can be prepared from three different starting materials although the iodide displacement is preferred ... 

Reactions of formyl complexes with alkylating agents can be more complex than the reductions in Eqs. (15-22). Some examples of simple hydride transfer exist. For instance, (CO)4Fe(CHO) (22) reduces octyl iodide to octane (75%) (27, 28) (C2H5)4N + 25 (Table I) reacts with heptyl iodide (overnight, room temperature, THF) to give heptane (71%) and (CO)4[(ArO)3P]Fe (37, 42) c/.s-(CO)5ReRe(CO)4(CHO) (19) converts octyl iodide to octane (68%) (47). 

Perfluorinated alkyl radicals, generated by photoinduction from heptadecafluoro-octyl iodide, were added to SWCNTs and the perfluorooctyl-derivatized CNTs obtained (Scheme 1.14). No difference in the solubility of the fluoroalkyl-substituted nanotubes and the starting materials was observed [148]. A pathway to the radical functionalization of CNTs sidewalls was predicted by classical molecular dy-... 

Holmberg showed that optically active alkyl halides are racemized in solution at rates which are second-order mixed with respect to halide ion and alkyl halide. By using 2-octyl iodide, Hughes and coworkcrs showed that the rate of exchange with radioactive 1 in acetone solution is precisely equal to the rate of inversion, both rates being mixed second-order. This, of course, is quite reasonable on the assumption that both reactions proceed by Sn2 mechanisms with inversion of configuration ... 

Yoon and Kim have prepared potassium triphenylborohydride (KPhjBH) and examined the reducing ability toward alkyl halides. n-Octyl iodide is reduced within 1 h at 0 °C, whereas n-octyl bromide takes 24 h for complete reduction. Secondary bromides are inert under these conditions. 

Other Alkylation Experiments. In other experiments lithium and sodium were used in place of potassium. Biphenyl and anthracene were used in place of naphthalene. 1,2-Dimethoxyethane was used in place of tetrahydrofuran. Butyl chloride, butyl bromide, butyl mesylate, butyl triflate, methyl iodide, and octyl iodide were used in place of butyl iodide. The conditions used in these experiments were very similar to the conditions used in the procedures described in the previous paragraphs. The isolation procedure was modified in those cases where the ionic salt, e.g., sodium iodide, was soluble in tetrahydrofuran. In these instances the tetrahydrofuran-soluble product was washed with water to remove the salt prior to further study. 

Table III. The Reduction and Alkylation of Illinois No. 6 Coal with Methyl, Butyl, and Octyl Iodide ...

The reaction of the. coal polyanion with methyl iodide occurs at least fivefold more rapidly than the reaction with butyl or octyl iodide, as judged by the rate of precipitation of potassium iodide. However, the results shown in the table reveal that there are only very minor differences in the solubility of the reaction products. In addition, we observed that the coal polyanions prepared from the insoluble residues of the first alkylation reaction were considerably more reactive. These polyanions reacted very rapidly with methyl iodide and reacted with butyl iodide to produce butene-1. 

The alkylation reactions of the coal polyanions also were investigated. The reactions of the polyanion with methyl, butyl, and octyl iodide were compared in tetrahydrofuran. The reaction could be monitored quite readily by the rate at which potassium iodide precipitated from solution. We estimate that methyl iodide is at least fivefold more reactive than butyl or octyl iodide under these conditions. This result, of course, suggests that the Sj 2 reactions of the coal polyanion are more... 

Alkylation of phthalimide anion can be carried out under solid-liquid phase-transfer conditions, using phosphonium salts or ammonium salts. In the reaction systems using hexadecyltributylphosphonium bromide, alkyl bromides and alkyl methanesulfonate are more reactive than alkyl chlorides. Octyl iodide is less reactive than the corresponding bromide and chloride. ( )-2-Octyl methanesulfonate was converted into (S)-2-octylamine with 92.5% inversion. Kinetic resolution of racemic ethyl 2-bromopro-pionate by the use of a chiral quaternary ammonium salt catalyst has been reported. Under liquid-liquid phase-transfer conditions, A -alkylation of phthalimide has been reported to give poor results. ... 

AA alkylating agent M methanol, E = ethyl iodide, B butyl iodide, 0 octyl iodide. 

Alkyl enol ethers can be conveniently prepared by the alkylation of a-methoxyvinyllithium and related metallated enol ethers. In a typical example, methyl vinyl ether (1) is converted by r-butyllithium to give a-methoxyvinyllithium (2). Reaction of (2) with octyl iodide gives the enol ether (3). Metallation of methyl propenyl ether (4) and methyl allenyl ether (5) can be similarly executed. ... 

Alkyl ketones can be prepared by the carbonylation of alkyl iodides in the presence of organoboranes. The carbonylation of iodocyclohexane with 9-octyl-9-BBN at 1 atm gives cyclohexyl octyl ketone in 65% yield[386]. This reaction is treated in Section 1.1.3.3. Methyl o-methylacetoacetate (919) is obtained by the reaction of the 2-bromopropionate 918, which has a /9-hydrogen, with CO and Me4Sn. PhjAs as a ligand gives better results than Ph3P[771]. 

Primary halides are more reactive than secondary compounds quaternary salt formation does not occur with tertiary halides, elimination always occurring to give the hydriodide and an olefln, Also, the larger the alkyl group the slower is the reaction this is shown by the very slow reaction of dodecyl bromide with quinoline, and even butyl iodide is much slower to react than methyl iodide. The longer chain primary halides commonly undergo elimination rather than cause quaternization for example, n-octyl and cetyl iodides give only the hydriodides when heated with 9-aminoacridine. ... 

Dimethyl-1,2,4-triazolium iodide with palladium acetate yields the carbene adduct 182 (97JOM(530)259). Under water it undergoes cis-trans isomerization to 183. Some other derivatives were reported in 1981 (81BCSJ800). 1,1 -Methylenebis(4-alkyl-l,2,4-triazolium)diiodides (alkyl = /-Pr, n-Bu, octyl) with palladium(II) acetate give the mononuclear complexes [L Pdl ] (99EJIC1965), where L2= l,l -methylenebis(4-R-l,2,4-triazol-2-ylidene) (R = /-Pr, n-Bu, octyl). Thermolysis of the products in THF gives the rran -dinuclear complexes 184... 

Hindered di-t-alkylamines RNHBu1 (R = t-Bu, t-octyl or 1-adamantyl) have been synthesized from t-alkylamines as follows. Reaction with peracetic acid gave the nitrosoalkanes RNO, which were treated with t-butyl radicals, generated from t-butylhydrazine and lead(IV) oxide, to yield t-butyloxyhydroxylamines. Reduction with sodium naphthalide in THF gave the products (equation 12). The di-t-alkyl-amines are inert to methyl iodide and dimethyl sulphate but can be alkylated by methyl fluorosulphonate42. 

For secondary alkyl iodides, the two one-electron polarographic waves are more separated. Reduction of 2-iodooctane at the potential of the first wave alfords the dialkylmercury and 7,8-dimethyl-tetradecane by reactions of the sec-octyl radical. At the potential of the second wave only octane and octenes are isolated [37]. 2-Bromooctane shows only one polarographic wave and yields octane and octene on reduction at any potential [37]. Radicals generated by reduction of primary and secondary iodoalkanes will react with other cathode materials including tin, lead and thallium to form metal alkyls [48,49],... 

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