Butyl iodide, reaction

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. ... 

Specifically, the reaction of trifluoromethyl radicals with carbon tetra-iodide produces perfluoro-tert-butyl iodide and perfluoroneopentane in the ratio of 3 1. Incomplete substitution is presumably due to steric factors around the crowded, central carbon atom. 

Regiospecific hydrocyanation of alkenes. Reaction of /-butyl isocyanide with the adducts of 1 with alkenes results in products (2) that are converted by iodine (excess) into hydrocyanides (3) and /-butyl iodide with release of ClCp2ZrI. (CH1).,SiN=C can be used in place of (CH,)3CN=C, but yields are generally lower.2... 

E Selective Wittig reagents. The reaction of 1 with lithium in THF provides LiDBP, which on reaction with an alkyl halide (2 equiv.) and NaNH2 in THF gives a salt-free ylide such as 2 or 3, formed by reaction with ethyl iodide or butyl iodide, respectively. These ylides react readily with aldehydes at —78°, but the intermediate oxaphosphetanes are unusually stable and require temperatures of 70-110° for conversion to the phosphine oxide and the alkene, which is obtained in E/Z ratios of 6-124 1. Highest (E)-selectivity is observed with a-branched aldehydes. 

Quite similar results have been found recently in the reaction of the cobalt(i) form of vitamin B,2 (Bus) with alkyl halides with n-butyl iodide, bromide and chloride, ethyl bromide and benzyl chloride the representative data point of vitamin B s falls several orders of magnitude above the outer sphere dissociative electron-transfer line (Walder, 1989). 

This simple view is clearly true for some reactions, e.g., the Diels-Alder dimerization of cyclopentadiene, where the rate constant in ethanol is the same as in hexane, and only a factor of three larger than in the gas phase. In contrast, for the example mentioned above of the 8 2 reaction (1), the reaction proceeds fifteen orders of magnitude faster in the gas phase than in methanol. For the Sfjl reaction of tert-butyl iodide, however, the gas phase rate constant can be estimated to be about 86 orders of magnitude slower than the solution phase rate constant. It is thus for ionic reactions that the tremendous changes in the rate constant upon solvation are seen. We are therefore specifically interested in those gas phase ion-molecule reactions that are the counterparts to the well-known solution phase reactions. 

Show by chemical equations the reactions involved in chain transfer by hexane, benzene, isopropylbenzene, propanol, butyl iodide, carbon tetrabromide, n-butyl... 

The H.T.-Cl can also be a catalyst for alkyl iodide production in toluene. Thus, benzyl iodide could be obtained by the reaction of benzyl chloride (33 mmol) with butyl iodide (33 mmol) at 373 K (Table 1). 

The hydrotalcite-1ike material catalyzes organic reactions in which the interlayer Cl" anions play the role of catalyst. The material catalyzed the halide-exchange reactions between benzyl chloride with butyl bromide or butyl iodide in toluene. The hydrota1cite-1ike material also catalyzes a disproportionation of trimethoxysilane to give silane and tetramethoxysilane. 

Diiodobutane has been prepared in 51% yield by the reaction of phosphorus, iodine, and tetrahydrofuran. It has also been prepared by the reaction of hydriodic acid with phenoxy-butyl iodide and with the diisoamyl ether of 1,4-butancdiol. ... 

A beautiful extension of this reaction has recently been communicated by Nozaki, Oshima, and Utimo-to.184 These workers simply admixed f-butyl iodide (3 equiv.), benzaldehyde (1 equiv.), methyl vinyl ketone (1 equiv.) and triethylborane (1 equiv.) in benzene (Scheme 60). After 5 min at 25 C, the reaction was subjected to standard extractive work-up and the crude product was purified by chromatography to give (54) in 63% yield. If methanol is substituted for benzaldehyde, the protonated product (55) is isolated in 79% yield. Although enones are equivalents of synthon (56), such a direct coupling of radical and ionic reactions had not been achieved previously. 

About 5% of the ethyl radical adduct was isolated in the reaction with r-butyl iodide and about 20% of the ethyl radical adduct was formed in the reaction with i-propyl iodide. These ratios compare quite well with those calculated by using the rate constants for halogen transfer in the above reference and the rate constants for addition of a primary radical to methyl vinyl ketone. 

The photolysis of aromatic species with tetranitromethane in perfluoro alcohol solvent has been studied, in which the radical cations were observed by EPR spectroscopy.284 Photo-stimulated reaction of 1- and 2-haloadamantanes and 1,2- and 1,3-dihaloadamantanes with various carbanionic nucleophiles afforded products rationalized through an SrnI mechanism.285 286 Photolysis of the cycloadduct formed between a functionalized derivative of C6o and diazomethane has been shown to afford a pah of ling-opened structures (125) and (126) via a proposed biradical intermediate (127) (Scheme 19). The UV-photolytic fragments of /-butyl iodide (T and /-Bu ) have been ionized by resonance-enhanced multiphoton ionization for TOF mass spectro-metric analysis.287 A two-dimensional position-sensitive detector provided angular distribution and translational energy data. 

Butyl iodide. Use 37 g (46 ml, 0.5 mol) of butan-l-ol together with the quantities of the other reactants used above a 2-hour reaction time is sufficient. The yield of butyl iodide, b.p. 129-130 °C, is 64 g (70%). 

Buchachenko (1974) has advanced another theory. He based his reasoning on the absence of the CIDNP signals for the reaction of //-butyl iodide with t-butyl lithium conducted in ether at -70°C. The halogen and metal quickly exchange under these conditions, but the C—C bond does not form. In contrast to the preceding scheme, Buchachenko s theory assumes that the radicals produced form complexes with the alkyl lithium associates. Alkyl... 

No reaction of unmilled aluminum powder with alkyl halides was observed during 10 hours of contact. When aluminum was milled with stainless steel balls in a stainless steel pot under helium at room temperature in the presence of butyl iodide for 8 min, an exothermic reaction was initiated and no more activation was required for the continuation of the reaction. 

If additional butyl iodide was injected into the mixture, the reaction continued without milling until aluminum was exhausted. Little gaseous product was evolved. The distillate of liquid product was colorless. 

Notice that for SN2 substitution, the alkyl halide came from the less sterically hindered group. For SN1 type reactions, the alkyl halide forms from the fragment of the original molecule that forms the more stable cation. Thus, the reaction of t-butyl ethyl ether with HI gives t-butyl iodide and ethyl alcohol. The following mechanism occurs ... 

---