Furan, 2-methyl

Bromochloromethane Methyl ether Methyl ethyl ether Methyl ethyl ketone Methyl formate 2-Methyl furan... 

The synthesis of phosphonium iodide 24, the precursor of phos-Br phorus ylide 12, begins with the alkylation of 5-lithio-2-methyl- furan,10 derived from the action of n-butyllithium on 2-methylfuran 17 (16), with 1,4-dibromobutane (17) to give 15 in 75% yield (see... 

Generating 6 from 6,6-dibromobicydo[3.1.0]hexane (35) with methyllithium in the presence of styrene, Moore and Moser [55] observed the first [2 + 2]-cycloaddi-tions of 6. Bottini et al. extended the variety of compounds able to trap 6 to 1,3-cyclo-hexadiene [54, 60], furan, 2-methyl furan, 1,3-cyclopentadiene and methyl-substituted 1,3-butadienes [54], In all these reactions, the dimer 38 of 6 is a byproduct or, as in the case of the less reactive trapping agents, even the main product. Hence it is advisable to use a reaction partner of 6, if it is a liquid, as the solvent. 

The propensity of the C5 site towards electrophilic substitution has been exploited to prepare functionalized oligomers by cationic polymerization. Thus monomers like isobutene, s ene, the vinyl ethers, etc. polymerize in the presence of simple furan derivatives such as 2-methyl furan to give essentially short chains (DP between 2 and 100 depending on the specific experimental conditions) with a terminal furan ring as a result of predominant transfer onto the C5 position of the added furan compound (20). 

Reduction of the alcohol group to produce 2-methyl furan can be achieved using a commercial Cu/Zn/Al/Ca/Na catalyst with the atomic ratio 59 33 6 1 1. This catalyst was found to achieve 99.7% conversion with 87.0% selectivity to 2-methyl fural at 250 °C. Hydrogenation from furfuryl alcohol yields a slightly higher selectivity of 92.7% at 98.1% conversion under similar conditions. 

Bierbach, A., I. Barnes, and K. H. Becker, Rate Coefficients for the Gas-Phase Reactions of Hydroxyl Radicals with Furan, 2-Methyl-furan, 2-Ethylfuran, and 2,5-Dimethylfuran at 300 + 2 K, Atmos. Environ., 26A, 813-817 (1992). 

Furan und 2-Methyl-furan reagieren mit N,N-Dialkyl-methaniminium-chloriden (auf ver-schiedenen Wegen hergestellt) in Acetonitril unter Dialkylaminomethylierung in 2- bzw. 5-Stellung1. 

Other compounds produced by this reaction having a meat-like odor were 4-mercapto-2-methyl-furan, 3-mercapto-2-methyl-4,5-dihy-drofuran, 4-mercapto-3-oxotetrahydrofuran, 3-mercapto-2-methyl thiophene and 3-mercapto-2-methyl-2,3-dihydrothiophene (50). 

Recently, a notable temperature-related effect was reported for site-selectivity (double-bond selectivity or chemoselectivity) in the PB reaction of unsymmetrically substituted furans (Scheme 7.14) [30]. For example, the selective formation of the more substituted oxetane, OX1, was observed during the PB reaction of 2-methyl-furan with benzophenone at a high temperature (61 °C). However, a 58 42 mixture of the oxetanes, 0X1 and 0X2, was reported at low temperature (—77 °C). This notable effect of temperature could be explained by the relative population of conformers of the intermediary triplet 1,4-biradicals, T-BR1 andT-BR2. The excited benzophenone was considered to attack the double bonds equally so as to produce a mixture of the conformers of T-BR1 and T-BR2 however, at low temperature the conformational change was suppressed. Thus, the site-random formation of oxetanes 0X1 and 0X2 was observed after the ISC process. Nonetheless, at high... 

Photochemical reaction in acetonitrile of 2 -deoxyuridine 5 -phosphate with the halo-heteroarenes 2-iodothiophene, 2-iodofuran, l-methyl-2-iodopyrrole and 3-iodothiophene affords the C-5 heteroaryl substituted nucleotides518.6-Aryluridines have been prepared by irradiation of 6-iodouridines in benzene, anisole, thiophene, Af-methylpyrrole or 2-methyl-furan in the presence of triethylamine519. 

High cycling efficiency is also obtained in LiAsF6-2Me-THF solutions containing 2-methyl furan [262], We attribute it mostly to the effect of Li doping by arsenic compounds, which in this case is not interfered with by pronounced solvent reactions [50], since 2Me-THF is one of the least reactive toward Li of all the commonly used solvents. 

PC = propylene carbonate DN = 1,3-dioxolane EC = ethylene carbonate 3-MeS-3 = methyl sulfolane DME = dimethoxy ethane THF = tetrahydrofuran S = sulfolane DMSO = dimethyl sulfoxide, DEE = diethyl ether, 2-Me-F = 2 methyl furan 2-MeDN = 2-methyl 1,3-dioxolane MA = methylacetate DMM = dimethoxymethane 2-MeOTHF = 2 methoxytetrahydrofuran BL = y-butyrolactone NM = nitromethane AN = acetonitrile MF = methyl formate DEC = diethyl carbonate DMC = dimethyl carbonate. 

N-Methyl formyl 2.6 difluoro benzamide lufenuron 2 Methyl furan carboxylic acid fenfuram... 

The yield of the process is in excess of 92 percent. The principal by-product is 2-methyl furan. Its formation increases when the reactor temperature is raised to compensate decreasing catalyst activity. At high temperatures, commercial quantities of 2-methyl furan can be produced. 

Figure 80. Formation of 2-Methyl Furan as a Function of Temperature. l-HARSHAWCu-1132 2 - CALSICAT X-407 TU 3 - Modified CALSICAT X-407 TU...

DIMETHYL-3-HYDROXY -2(5H)-FURANON 3-HYDROXY-4-METHYL-5-ETHYL 2(5H)-FURANON FURFURYL-MERCAPTANE 2-METHYL FURAN-3-THI0L... 

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