Ferf-butylbenzene

Kinetic data are available for the nitration of a series of p-alkylphenyl trimethylammonium ions over a range of acidities in sulphuric acid. - The following table shows how p-methyl and p-tert-h xty augment the reactivity of the position ortho to them. Comparison with table 9.1 shows how very much more powerfully both the methyl and the tert-butyl group assist substitution into these strongly deactivated cations than they do at the o-positions in toluene and ferf-butylbenzene. Analysis of these results, and comparison with those for chlorination and bromination, shows that even in these highly deactivated cations, as in the nitration of alkylbenzenes ( 9.1.1), the alkyl groups still release electrons in the inductive order. In view of the comparisons just... 

Chemical Name ferf-butylbenzene CAS Registry No 98-06-6 Molecular Formula C10H14, C6H5C(CH3)3 Molecular Weight 134.218 Melting Point (°C) ... 

The ions Sm+, Eu+, Tm+, and Yb+ form addition complexes with 1,3,5-tri-ferf-butylbenzene (130), whereas other lanthanide ions form dehydrogenation products (see Section III.A.2). 

It is proposed that 32 reacts from its nn excited state by the nitro-to-nitrite (33) inversion followed by nitrite homolysis, when the naphthoxy radical must diffuse away from the cages to obtain the dimerization intermediate 35. However, the source of oxidizing agents is not identified. In comparison, o-nitro-ferf-butylbenzenes 37 are excited to undergo intramolecular H-atom transfer and cyclization to give indol-IV-oxides 40 (equation 34)38. The discrepancy may arise from the nature of the excited state, e.g. that of 37 may react from its njr state. 

Naphthylamine Toxaphene Dimethyl phthalate Butylbenzene sec-Butylbenzene ferf-Butylbenzene Isobutylbenzene... 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Butylbenzene, see Butylbenzene f -Butylbenzene, see Isobutylbenzene n-Butylbenzene, see Butylbenzene s-Butylbenzene, see sec-Butylbenzene secondar/-Butylbenzene, see sec-Butylbenzene f-Butylbenzene, see ferf-Butylbenzene ferffar/ Butylbenzene, see ferf-Butylbenzene Butyl benzyl phthalate, see Benzyl butyl phthalate n-Butyl benzyl phthalate, see Benzyl butyl phthalate Butyl cellosolve, see 2-Butoxyethanol n-Butyl cellosolve, see 2-Butoxyethanol Butylene, see 1-Butene 1-Butylene, see 1-Butene... 

Dimethylethene, see 2-Methylpropene (1,1-Dimethylethyl)benzene, see ferf-Butylbenzene uns/m-Dimethylethylene, see 2-Methylpropene Dimethylethylmethane, see 2-Methylbutane Dimethylformaldehyde, see Acetone Dimethylformamide, see Dimethylformamide... 

Methyl-l-phenylpropane, see Isobutylbenzene 2-Methyl-2-phenylpropane, see ferf-Butylbenzene Methyl phthalate, see Dimethyl phthalate... 

Phenylpropane, see Isopropylbenzene 2-Phenylpropene, see a-Methylstyrene p-Phenylpropene, see a-Methylstyrene 2-Phenylpropylene, see a-Methylstyrene p-Phenylpropylene, see a-Methylstyrene o-Phenylpyrene, see Indeno[l,2,3-caf p3U ene Penyltrimethylmethane, see ferf-Butylbenzene Philex, see Trichloroethylene... 

Trimethylnorcamphor, see Camphor Trimethylphenylmethane, see ferf-Butylbenzene Tri-2-methylphenyl phosphate, see Tri-o-cresyl phosphate 1,1,1-Trimethylpropane, see 2,2-Dimethylbutane... 

Steele, W.V., Chirico, R.D., Knipmeyer, S.E., and Nguyen, A. Vapor pressure, heat capacity, and density along the saturation line measurements for benzenamine,butylbenzene, sec-butylbenzene, ferf-butylbenzene, 2,2-dimethylbutanoic acid, trideca-fluoroheptanoic acid, 2-butyl-2-ethyl-l, 3-propanediol, 2,2,4-trimethyl-l, 3-pentanediol, and l-chloro-2-propanol, J. Chem. Eng. Data, 47(4) 648-666, 2002a. 

ESR spectroscopy and ferf-butylbenzene as the solvent if not otherwise stated. Quasi-equilibrium method (see text) and chlorobenzene as the solvent. 

The alkylation product of benzene (W) and ferf-butylbenzene (S4) with ethylene yields predominantly sec-butyl alkylates. This is the case because the ethylbenzene alkylate formed reacts very rapidly in the normal side-chain alkylation reaction. The sec-butyl aromatic alkylates much less readily. The much greater ease of side-chain alkylation over nuclear alkylation also accounts for the exclusive formation of side-chain alkylates from compounds, such as cumene, that are predominantly metalated on the ring by alkylalkali metal compounds. 

Tables I and II include data for the co-oxidations of styrene and butadiene in chlorobenzene and ferf-butylbenzene solutions, as well as with no added solvent. These solvents were chosen because the rate of oxidation of cyclohexene varies significantly in them at the the same rate of initiation (6). There is a variation in the over-all rate of oxidation under these solvent conditions, but there appears to be no significant difference in the measured ra and rb (Table II). If the solvent does affect the propagation reaction in autoxidation reactions, it affects the competing steps to the same degree.

Materials. Cumene and Tetralin were purified by extraction with concentrated sulfuric acid, until the extracts were colorless, then with 2N caustic soda and distilled water, and finally dried and distilled. Both were stored in darkness under No and percolated through silica gel immediately before use. ferf-Butylbenzene (99.9% by GLC) was used as an inert diluent for cumene and Tetralin where indicated. Squalane (M and B Embaphase) was used as received. AIBN was recrystallized from ether and had a melting point of 102°-103°C. Metal dialkyl dithiophos-phates were prepared as described previously (6) zinc diisopropyl dithio-phosphate was finally recrystallized twice from n-heptane and had a melting point of 146 °C. 

Table I. AIBN-Initiated Oxidation of Organic Phosphorus Compounds in ferf-Butylbenzene at 70°C.

C-H Insertion versus Double-Bond Addition in the Reaction of Carbon with Aromatics. The factors that determine if C atoms react with an aromatic by C—H insertion or DBA are not yet understood. Benzene and substituted benzenes are postulated to react by C—H insertion although detailed labeling studies have only been carried out in benzene, toluene, and ferf-butylbenzene. No C—H insertion is observed in the reaction of carbon with 71, while C—H insertion is a minor pathway when carbon reacts with 76 and 87. 

One cannot help being impressed by the dominant character of the methyl group. It would seem that when the electron release of the methyl groups is balanced across the benzene nucleus the knock resistance is increased this indicates that the velocity of combustion is slowed down. On the other hand, when the electron releases of the methyl groups supplement each other, as in the case of the vicinal derivatives, knock resistance is decreased this indicates that the combustion velocity is increased. An accumulation of methyl groups either upon the side chain, as in ferf-butylbenzene, or upon the nucleus, as in isodurene, seems to increase the knock resistance. 

Even ferf-butylbenzene reacts satisfactorily (86% yield) without de-tert-butylation. Acylation of p-xylene with benzoic acid gave 71% yield with continuous removal of water. Water removal was also the decisive factor in producing anthraquinones with phthalic anhydride in satisfactory yields (52-89%). 

SAMPLE SOLUTION (a) Friedel-Crafts alkylation of benzene with isobutyl chloride is not suitable, because it yields ferf-butylbenzene by rearrangement. 

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