Indane, 1-butyl

Bis(dichloroaluminum)phenylimide, 202 f-Butyl hydroperoxide-Dichlorotris-(triphenylphosphine)ruthenium(II), 54 Di-f-butylimoxyl, 94 a-Methylbenzylamine, 185 Pivaldehyde, 249 Indans (see Arenes)... 

Another approach to the problem involves the study of molecules in which one side is more accessible for adsorption than the other one. This feature is to a certain extent present in 2-t-butylindane which would be predicted to form substrate-electrode complex 15 preferentially. On anodic acetoxylation of 2-t-butyl-indane a mixture of cis- and r/vz s-l-acetoxy-2-t-butylindane in the proportions 16 84 is formed 106 Vhi all probability via a carbonium ion mechanism (Eq. 

Table 19 shows results from the a-acetoxylation of two 2-alkyl-indans under different conditions analogous homogeneous reactions are included for comparison. Table 19 demonstrates that, at most, a weak effect is noticeable in the case of 2-t-butylindan, in that anodic oxidation on platinum, a strongly adsorbing metal, gives a cis/trans ratio that is about 10 times that observed from a 2-t-butyl-1-indanyl cation generated by solvolysis. Ratios on the weaker adsorbing electrode materials, carbon and lead dioxide, fall in between. For a smaller substituent (R = methyl) no effect is observable. 

The anionic form usually obtained in using enamines as synthesis reagents is usually the allyl form. Thus, Blomquist and Moriconi46" showed that, by reacting a solution of the pyrrolidine enamine of indan-2-one in tetrahydrofuran with w-butyl lithium in -hexane at —65 °C (equation 22), the proton removal is complete in about 10 min. 

Borsenberger et al. (1995a) measured electron mobilities of PS doped with a series of acceptor molecules 2-r-butyl-9,10-N,N -dicyanoanthraquinone-diimine (DCAQ), 2-methy 1-2-pentyl-1,3-bis(dicyanomethylene)indane (DCMI), 3,5-dimethyl-3, 5 -diisopropyl-4,4,-diphenoquinone (DPQ-A), N,N -bis(l, 2-di-methylpropyl)-l,4,5,8-naphthalenetetracarboxylic diimide (NTDI), and 1,1-dioxo-2-(4-methylphenyl)-6-phenyl-4-(dicyanomethylidene)thiopyran (PTS). The reduction potentials are -0.22, -0.34, -0.45, -0.56, and -0.15 V, respectively. The dipole moments are between 0.30 and 4.0 Debye. In all materials, the field and temperature dependencies were described as logu oc pE1/2 and -(T0/rP)2. Figure 33 shows the results for 40% NTDI doped PS. The results... 

The importance of stereoelectronic effects has been assessed quantitatively by comparing the CH3/CH2CH3 and CH3/CH2tBu reactivity ratios (statistically corrected) in the radical cations of p-ethyltoluene (ETT), p-neopentyltoluene (NPT), 5,6-dimethylindane (DMI), and 2,2,5,6-tetramethylindane (TMI) (Scheme 35) [148], In the two indane derivatives the methylene groups in positions 1 and 3 bear a substituent which resembles an ethyl and a t-butyl group, respectively. In the p-xylene series, on going from ETT + to NPT"" a dramatic 1400-fold decrease in reactivity is observed for deprotonation from the methylene position, behavior which is readily explained on the basis of a stereoelectronic effect (see above and Scheme 34). 

Influence of the Tri(t i t-butyl)silyl Substituents on the Molecular Structures of Phosphanylalanes, -gallanes and -indanes... 

EC>urEC12 a few alkylbenzenes (n-butyl-, n-pentyl-, a trimethyl-, and other multisubstituted), indans, and naphthalene... 

When the latter reaction was discovered, Kazanskii and Liberman (755, 154) systematically investigated the dehydrocyclization of alkyl-substituted benzenes indane, 1-methylindane, and 2-methylindane were obtained from n-propyl-,. sec-butyl-, and isobutylbenzenes, respectively (Scheme 79). 

Alcohol 3 (solid) (1 mmol) and 5% of iodine (0.05 mmol, 12.7 mg) were triturated in a glass mortar for 1 min, transferred to a 15-mL flask and heated at 70 °C for 3 h. an aqueous solution of Na2S203-5H20 (10%, 20 mL) was then poured into the cooled mixture and the crude product was extracted with tert-butyl methyl ether (35 mL) and washed with water. Pure l,l,3-trimethyl-3-phenyl-indane (5, colorless oil) was obtained by column chromatography (Si02, hexane-CH2C12 4 1) in 91% yield. 

Indan-[Pg.930]

Fig. 1. Oxidation of mixtures of cumene and aralkyl hydrocarbons at 90°C, 0.02 M f-butyl perbenzoate. A, Dibenzyl ether B, indan C, diphenylmethane D, ethylbenzene E, theoretical for an inert diluent. Reprinted with permission from ref. 139. Copyright by the American Chemical Society.

Another experimental result is also consistent with the hypothesis that cyclic 1,2,3-triketones are not stable. 2-Diazoindan-l,3-dione (9.91) is oxidized by eA butyl hypochlorite in ethanol to the 2-monoacetal 9.92 of indan-l,2,3-trione. The monoacetal undergoes hydrolysis to 2,2-dihydroxyindan-l,3-dione (ninhydrin hydrate 9.93), but the trione itself could not be identified (9-41). 

The signal observed at 5 = 314.2 ppm in the C NMR spectrum is the most deshielded signal ever observed for a carbene center. [27] The carbene 50 is stable for days in solution at -50°C but undergoes a classical C-H insertion reaction at room temperature within a few hours, the 4,6-di-tert-butyl-l,l-dimethyl-3-(methyl-fert-butylamino)indan 51 was obtained as the major product. [65]... 

Y = F) with sodiiun methoxide, but undergoes ring-opening with potassium hydroxide in t-butyl alcohol to give the acid o-C F4H-CF CF-C02H, whidi is converted into the dichloro-compound o-CsFaH-CFCl-CFCl-COaH by treatmmt with phosphorus pentachloride followed by hydrolysis. Both 3-chloroh tafluoro-and octafluoro-indene are converted into the oxo-sulphonic add (32) by 20% oleum, and the dibromide (33a) or the nitro-indane (33b) is formed when octa-fluoioindene reacts with bromine or HNOa-HF, respectively. The fomiation of the antiaromatic cabocation (34) when octafluoroindene dissolves in SbFs-SOa at -40°C has been briefly studied by n.m.r. spectroscopy. ... 

Ethanol, 2-[(1,7,7-trimethylbicyclo [2.2.1] hept-2-yl) oxy], exo-. See (exo)-2-Camphanyl-P-hydroxyethyl ether Ethanol, undenatured. See Alcohol Ethanone, 1-(2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl)-. See Acetyl hexamethyl indan Ethanone, 2,2-dimethoxy-1,2-diphenyl-. See 2,2-Dimethoxy-2-phenylacetophenone Ethanone, 1-(4-(1,1-dimethylethyl)-2,6-dimethyl-3,5-dinitrophenyl)-. See Musk ketone Ethanone, 1-[4-(1,1-dimethylethyl) phenyl]-. See p-t-Butyl acetophenone Ethanone, 1-(4-ethylphenyl)-. See4-Ethylacetophenone... 

C, H only (13) Cyclo-(propyl, butyl, hexyl), indane, naphthalene, fused benzenes... 

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