Butyl chloride, oxidation

A successful procedure for the formation of 2,5-di-t-butylfuran involves reaction of the parent heterocycle with f-butyl chloride in the presence of iron(III) chloride and iron(III) oxide. Iron(III) oxide acts as a hydrogen chloride scavenger and at the same time regenerates the catalyst. Concurrent polymerization normally deactivates the catalyst (82CI(L)603). 

Trimethylpyrylium perchlorate has been prepared from 2,6-dimethylpyrone and methylmagnesium halides 6 from mesityl oxide and sulfoacetic acid 6 from mesityl oxide (or less satisfactorily from acetone) and a mixture of acetic anhydride and perchloric acid 7 from mesityl oxide, acetyl chloride, and aluminum chloride 8 and from <-butyl chloride, acetyl chloride,... 

Chromyl chloride also oxidizes saturated hydrocarbons. For example, it oxidizes isobutane to tert-butyl chloride ... 

In another simple procedure, deprotonation of methoxy bis(trimethylsilyl)methane with butyl lithium and addition of the resulting anion to aldehydes induces Peterson elimination (Scheme 27). The product methyl enol ethers could be hydrolysed to the parent acyl silanes with hydrochloric acid-THF or could be treated with electrophiles such as M-halosuccinimides to give a-haloacyl silanes105. Alternatively, treatment with phenyl selenenyl chloride, oxidation at selenium and selenoxide elimination afforded a,/3-unsaturated acyl silanes. 

Concomitant encapsulation also allows the reciprocal interaction between two different chiral guests. In the achiral cylindrical capsule 1111, encapsulation of (R)-styrene oxide with racemic ( )-2-butyl chloride or the alcohols ( )-2-butanol or ( )-2-pentanol showed two coencapsulation diastereoisomeric complexes comprising the enantiopure oxide and one enantiomer of the secondary guest. Unfortunately, these combinations did not provide any... 

With regard to the sulfmyl chlorides needed for sulfinate ester synthesis, a large number of them are readily accessible by oxidation of the corresponding disulfide according to the Young and Herrmann procedure."4 However, in the case of the more hindered ferf-butyl chloride, Netscher and Prinzbach s method gives better... 

For Zr( j -Cp)2(HXR), generation of Zr(Cp- )2 by phosphine-induced reductive elimination followed by treatment with n-butyl chloride gives the desired oxidative addition product, which is stable ... 

Polyoxyl 10 Oleyl Ether Free Ethylene Oxide Stainless Steel, 1.8 M x 3 mm I.D. (OD) S3 Helium 160 FID n-Butyl Chloride NF (19, p. 2498)... 

Other oxidants of hexavalent chromium are chromyl chloride and di-/er/-butyl chromate. Chromyl chloride adsorbed on alumina-silica gel from its solution in dichloromethane oxidizes aliphatic and aromatic alcohols at room temperature within hours in 77-100% yields [675]. Di-tert-butyl chromate, prepared in situ from chromyl chloride in tert-butyl alcohol at -70 °C, gives comparable results under similar conditions [674. Di-tert-butyl chromate, prepared from chromium trioxide and tert-butyl alcohol, oxidizes primary aliphatic and aromatic alcohols to the corresponding aldehydes even at low temperatures (1-2 °C) [677, 678]. 

Lead tri-n-butyl chloride is obtained from magnesium butyl iodide, and lead chloride, the product being treated with hydrogen chloride as above. It forms colourless, flat needles which melt to a clear liquid at 109° to 110° C., and have a similar solubility to the propyl compound. The hydroxide is prepared by dissolving the chloride in aqueous alcohol and shaking with silver oxide. The solution in water ha an alkaline reaction, and absorbs carbon dioxide from the air. When treated with hydrogen bromide a white precipitate of lead iri-n-butyl bromide separates, which may be recrystallised from ether or chloroform. 

Substituted alkyl halides undergo, of course, the reactions characteristic of their other functional groups—nitration of benzyl chloride, oxidation of ethylene bromohydrin, addition to allyl bromide —but as halides they react very much like ethyl or isopropyl or /cr/ butyl halides. 

Tri(phenylthio)methyllithiuin does not react properly with less reactive electrophiles such as n-butyl chloride, 2-iodopropane (Scheme propylene oxide (Scheme and especially cyclo-... 

The very rapid oxidation of phenols by solvent radical cations can be expected to yield phenol radical cations as the first products. These species are short-lived, except in highly acidic solutions, and were not observed in the microsecond pnlse radiolysis experiments described above. They were detected, however, in frozen matrices and with nanosecond pulse radiolysis Gamma irradiation of phenols in w-butyl chloride or in l,l,2-trichloro-l,2,2-trifluoroethane (Freon 113) at 77 K produced phenol radical cations, which were detected by their optical absorption and ESR spectra . Annealing to 133 K resulted in deprotonation of the radical cations to yield phenoxyl radicals. Pulse radiolysis of p-methoxyphenol and its 2,6-di-fert-butyl derivative in w-butyl chloride at room temperature produced both the phenol radical cations and the phenoxyl radicals. The phenol radical cations were formed very rapidly k = 1.5 x 10 ° M s ) and decayed in a first-order process k = 2.2 x 10 s ) to yield the phenoxyl radicals. The phenoxyl radicals were partially formed in this slower process and partially in a fast process. The fast process of phenoxyl formation probably involves proton transfer to the solvent along with the electron transfer. When the p-methoxy group was replaced with alkyl or H, the stability of the phenol radical cation was lower and the species observed at short times were more predominantly phenoxyl radicals. 

Neohexene is by far the more expensive of the two starting materials, and so the process shown in Scheme 4.45 is unsatisfactory, since it consumes twice as much of this reagent as is desirable. One way of overcoming this problem is to add a sacrificial oxidant that is less expensive than neohexene. For example, /-butyl chloride, under the influence of aluminium chloride, loses its chlorine to produce the /-butyl cation, which can abstract the hydride ion from p-cymene and thus save one molar equivalent of neohexene. 

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