2.3- dimethylbutane, oxidation

Grignard reaction with formaldehyde closer to our desired product. Subsequent hydrolysis will yield 2,2-dimethylbutanol our desired product is 2,2-dimethylbutanal. Oxidation of the primary alcohol to the aldehyde can be accomplished with Sarett s reagent, a combination of chromium trioxide (CrOs) with pyridine. 

A. Ciszewski and G. Milczarek, Electrocatalysis of NADH oxidation with an electropolymerized film of l,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane. Anal. Chem. 72, 3203-3209 (2000). 

Photolytic. Major products reported from the photooxidation of 2,3-dimethylbutane with nitrogen oxides are carbon monoxide and acetone. Minor products included formaldehyde, acetaldehyde and peroxyacyl nitrates (Altshuller, 1983). Synthetic air containing gaseous nitrous acid and exposed to artificial sunlight (A. = 300-450 nm) photooxidized 2,3-dimethylbutane into acetone, hexyl nitrate, peroxyacetal nitrate, and a nitro aromatic compound tentatively identified as a propyl nitrate (Cox et al., 1980). 

Biethylene oxide, see Tetrahydrofuran Bihexyl, see Dodecane Biisopropyl, see 2,3-Dimethylbutane Bilorin, see Formic acid... 

UN 1206, see 3,3-Dimethylpentane Heptane UN 1208, see 2,2-Dimethylbutane, 2,3-Dimethylbutane, Hexane, 2-Methylpentane UN 1212, see Isobutyl alcohol UN 1213, see Isobutyl acetate UN 1218, see 2-Methyl-l,3-butadiene UN 1220, see Isopropyl acetate UN 1221, see Isopropylamine UN 1224, see 3-Heptanone, 2-Hexanone, Isophorone UN 1229, see Mesityl oxide UN 1230, see Methanol UN 1231, see Methyl acetate UN 1232, see 2-Butanone UN 1233, see sec-Hexyl acetate... 

A highly reactive CM-bis(imido)ruthenium(VI) complex has been suggested in the oxidation of cii-[Ru(bpy)2(tmen)] (tmen = 2,3-dimethylbutane-2,3-diamine) by Ce in aqueous solutions. This Ru species decomposes rapidly in water to give [Ru(bpy)2 (ONCMe2CMe2NO)] ". ... 

One of the most efficient methods for oxidation of primary alcohols to either aldehydes or carboxylic acids is the one, commonly known as the Anelli oxidation. This reaction is carried out in a two-phase (CH2Cl2/aq.buffer) system utilizing TEMPO/NaBr as a catalyst and NaOCl as the terminal oxidant The new system described here is an extension of the Anelli oxidation, but surprisingly, does not require the use of any organic solvents and replaces the KBr co-catalyst with the more benign, Na2B40y (Borax). The use of the new cocatalyst reduces the volume of the buffer solution and eliminates completely the need of a reaction solvent. The new system was successfully applied in the industrial synthesis of the 3,3-Dimethylbutanal, which is a key intermediate in the preparation of the new artificial sweetener Neotame. 

The exchange of a number of compounds in this category with deuterium has been examined by Burwell and his colleagues. n-Heptane has been exchanged over nickel-keiselguhr (43), reduced nickel oxide (29), a series of nickel catalysts of varying crystallite size (37), and over palladium supported on 7-alumina (43). Less extensive studies were also made with 2,3-dimethylbutane (29, 43) and n-hexane (42). 

The extremely hindered manganese(III) tetra(2,4,6-triphenylphenyl)porphyrin acetate [Mn(TTPPP)OAc], in contrast, gives the less hindered 3,3-dimethylbutane-l-ol with exceptionally high selectivity. Hindered metalloporphyrins also exhibit an increasing reactivity in the oxidation of the -1 CH2 site in straight-chain alkanes.148... 

Figure 4. Effect of oxygen concentration on ionization during oxidation of 2,2-dimethylbutane...

When a stream of oxygen containing 15% ozone was passed through a solution of isobutane in HSC F-SbFs-SOiClF solution held at —78°C, the colorless solution immediately turned brown in color. 1H and 13C NMR spectra of the resultant solution were consistent with the formation of the dimethylmethylcar-boxonium ion in 45% yield together with trace amounts of acetylium ion (CH3CO+). Further oxidation products (i.e., acetylium ion and C02) were reported to be observed in a number of reactions studied. Such secondary oxidation products, however, are not induced by ozone. Similar treatment of isopentane, 2,3-dimethylbutane, and 2,2,3-trimethylbutane resulted in formation of related carboxonium ions as the major products (Table 5.37). 

Oxidation of 2,3-dimethylbutane-2,3-bis-hydroxylamines with bromine or sodium periodate in aqueous solution at room temperature yielded 3,3,4,4-tetramethyl-A1-l,2-diazetine-l,2-dioxide <1972JA5077, 1975JOC1409> which can be reduced to diazetidine. 

The gas phase oxidation of 2,3-dimethylbutane (Table 7, entry 51) leads to number of products even under mild conditions [56], The selectivity of alkane oxidations, e.g. methane oxidation (Table 7, entry 52) increases substantially in the pres-... 

Bis(hydroxyamino)-2,3-dimethylbutane (160) and glyoxal gave 2,2,3,3-tetramethyl-2,3-dihydropyrazine 1,4-dioxide (161) (H20—EtOH, reflux, 10 min 83% naturally not subject to facile oxidation).702 Also other examples.1,86 237 414,466,483 588 988 1108... 

Aliphatic gem-dihalides require more vigorous conditions for hydrolysis than do the benzal halides. Examples are found in the treatment of certain 1,1-dichloroalkanes, like l,l-dichloro-3 methylbutane and 1,1-dichloro-3,3"dimethylbutane, with water and, in some cases, magnesium oxide for 4 hours at 200-300°. The aldehydes are formed in 60-96% yields (cf. method 222). 

Oxidation of the pyrazole carboxaldehydes 294 using potassium permanganate in aqueous pyridine gave satisfactory yields of the carboxylic acids 295 (Equation 56) <2001CHE467>. Condensation of AT-alkylpyrazole-4-carbaldehyde 296 with 2,3-bis(hydroxyamino)-2,3-dimethylbutane sulfate, then sodium periodate oxidation of 1,3-dihydroxyimi-dazolidine 297 afforded pyrazolyl nitronyl nitroxides 298 (Scheme 26) <2001ARK55>. Another approach to... 

Four other alkanes were photolyzed in the presence of nitrous oxide principally to determine the yield of N2. In all four cases < (N2) was less than for cyclohexane solutions (Table II and Figure 1). For cyclopentane and 2,2-dimethylbutane < (N2) at 68 mM N20 is only 0.04, which is 10% of the yield of N2 for cyclohexane. For 2,2,4-trimethylpen-tane solutions (N2) is also low, and (CH4), a major product, is unaffected by N20. n-Hexane seems to be an intermediate case with respect to No formation like cyclohexane ( N2) + < ( H2) 1 here too. 

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