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XCVI.-The F&Del- Crafts' Reaction Applied to Htapl,,- Alkyl Halides. Pi

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XCVI.-The F&Del- Crafts' Reaction Applied to Htapl,,- Alkyl Halides. Pi View Article Online / Journal Homepage / Table of Contents for this issue FRIEDEL-CRAFTS’ REACTION APPLIED TO ISAPHTBALENE. 1141 XCVI.-The F&del- Crafts’ Reaction Applied to hTapl,,- thalene. The Action of Di-,Tri-, and Tetra- alkyl Halides. Pi*epaiwtion of apa’p’-Diszaphth- anthracene.* By ANNIEHOMER, B.A. (Fellow of Newnham College, Cambridge). A STUDY of the literature dealing with the applications of the Friedel-Crafts’ reaction to mixtures of naphthalene with the di-, tri-, and tetrtlrhalogen derivatives of methane and ethane reveals the existence of many contradictory statements and of much frag- mentary data. As the development of the author’s previous work (Trans., 1907, 91, 1103) necessitated the use of this reaction, a revision and extension of much of the published work was under- taken. Whilst the typical course of the reaction is represented by the equation : RH+R’Cl=RR’+HCl . (i), it was observed that when naphthalene is used, this reaction is accompanied by others, a discrepancy which is explained by reference to the demonstration by Friedel and Crafts (Compt. rend., 1885, 100, 692) that when aluminium chloride acts on benzene, toluene, or naphthalene alone, condensation occurs in accordance with the equation : RH+RH=RR+H, . ._b . (ii). The work about to be described shows that in the condensation of an aromatic hydrocarbon with a halogen derivative of a paraffin, reactions (i) and (ii) occur simultaneously, the difference between the reaction velocities being greatly affected by the temperature. But whilst with benzene and its homologues reaction (ii) proceeds Published on 01 January 1910. Downloaded by Middle East Technical University (Orta Dogu Teknik U) 12/02/2016 20:08:00. with a negligibly small velocity below 160°, with naphthalene it occurs to an appreciable extent even at 80°, and at higher temperatures becomes the main reaction. The concordant results of previous investigators have shown that the alkyl halides react with naphthalene and aluminium chloride according to equation (i), the only exception being methyl chloride, which the author of this paper has investigated. The present work is therefore confined to the condensation of the hydrocarbon with (a) as-dichloroethane, (6) methylene chloride, (c) ethylene bromide, (d) chloroform, (e) s-tetrachloro- and tetrabromo-ethane, and (f) nickel carbonyl. The condensation (e) was of special importance as promising a means of obtaining the dinaphthanthracene, C22H14, * This paper corresponds with tho two abstracts in Proc., 1910, 26, 11, 12. View Article Online 1142 HOMER : THE FRIEDEL-CRAFTS’ prepared by Hartenstein (Diss., Jena, 1892), a specimen of this substance being required for the study of its absorption spectrum in connexion with the investigation of the constitution of the tetra- methylpicene previously prepared by the author (Homer and Purvis, Trans., 1908, 93, 1319); eventually Prof. E. von Meyer kindly supplied a specimen of Hartenstein’s preparation. The condensations described in the present paper were performed in each case by treating the mixture of paraffin halogen compound and naph€halene, in theoretical proportion, with aluminium chloride not exceeding in weight 20 per cent. of the naphthalene used. Since it was soon found that rise in temperature in the initial stages favours reaction (ii) and leads to the production of PP-di- naphthyl, the condensation, whenever possible, was allowed to proceed in the cold for one or two days; the tarry product, after being heated for one and &half hours to the boiling point of the alkyl halide, while still hot was treated with hydrochloric acid and water. After half an hour the mass was extracted with benzene and the solvent separated from the extract by distillation; the residues were then fractionally distilled under (A) ordinary and (B) diminished pressure, and the fractions systematically examined as indicated below. (a) Interaction of as-Dichloroethane and Naphthalene. From the products of this reaction, Bodroux (Bull. SOC.chim., 1901, [iii], 25, 491) isolated the a- and P-methyl- and ethyl- naphthalenes and f@-dinaphthyl. The violence of the reaction, which sets in immediately, has to be modified by adding the aluminium chloride gradually and by external cooling. In the present work it has been shown that-: (A) Distillation under ordinary pressure yielded three fractions : Fraction i consisted of naphthalene. Published on 01 January 1910. Downloaded by Middle East Technical University (Orta Dogu Teknik U) 12/02/2016 20:08:00. Fraction ii gave on redistillation a portion boiling at 243-245O. The crystals deposited from this solution on cooling yielded a picrate melting a€ 114O when crystallised from benzene, and at llOo when crystallised from alcohol, the analysis of which showed it to be the P-methylnaphthalene obtained by Bodroux. Fraction iii, which distilled at the temperature at which the glass began to soften, was obtained as a dark viscous oil, giving a crystalline deposit, which, after washing with petroleum and crystallisation from benzene, melted at 180-18Z0 ; analysis of the picrate which melted at 183O showed this substance to be B8-d;- naphthyl. It was observed that during the distillation of the products of the reaction active decomposition was taking place, a fact not noted by Bodroux. View Article Online REACTION APPLIED TO NAPHTHALENE. 1143 (B) Distillation under diminished pressure yielded three fractions. Fraction i (below 250°/ 20 mm.) yielded on redistillation under 760 mm. pressure naphthalene and a little of an oil boiling at 240-260° ; the oil was probably a mixture of methylnaphthalenes, and was not further examined. Fraction ii (250°/20 mm.) was a highly fluorescent oil the pro- duction of which had been noted by Bodroux, who, however, did riot attempt to isolate any pure substance from it. After repeated distillation and long keeping, this oil solidified completely, and on repeated crystallisation from hot alcohol colourless, non-fluorescent needles melting at 90.5O were obtained, which agrees closely with the melting point of dinaphthylmethane, given as 92O (Richter, Ner., 1880, 13, 1728). The fluorescent oil and the crystals had the same composition, as shown by the corresponding analyses I and I1 : I. 0.2903 gave 0.9938 CO, and 0.1635 H,O. C=93.38; H=6*31. 11. 0.1036 ,, 0.3548 CO, ,, 0.0597 H,O. C= 93.42 ;H = 6.47. M.W. by cryoscopic method in benzene=255.6 and 262.6. C,,H,, requires C = 93-97; H = 6.03 per cent. M.W. = 268. The identity of this compound with Richter’s was conclusively proved by analyses of its derivatives. On analysis of the brome derivative : 02389 gave 0.5185 CO, and 0.0763 H,O. C =59.19; H = 3.56. 0.2195 ,, 0,1922 AgBr. Br=37.27. C21H14Br2requires C = 59.15 ; H = 3-29; Br = 37.55 per cent. On analysis of the nitro-compound : 0.1505 gave 0.3083 CO, and 0.0438 H,O. C = 55.9 ; H = 3-26. 0.1455 ,, 14.92 C.C. N, (moist) at 1l0and 748.4 mm. N=12*23. C21H12(N02)4requires C = 56.2 ;H = 2.68 ;N = 12.5 per cent. Published on 01 January 1910. Downloaded by Middle East Technical University (Orta Dogu Teknik U) 12/02/2016 20:08:00. The formation of PP-dinaphthylmethane (C2,H,,) rather than of dinaphthylethane, C22H18,is probably explained by Bodroux’s observation that methane and hydrogen chloride are evolved during the earlier stages of the condensation ; possibly the latter hydro- carbon is first formed and subsequently converted into methane and BB-dinaphthylmethane by the hydrogen evolved by the action of the aluminium chloride, thus: CHMe(C,,Hi), + 2H = CH, + CH,(C,,H7)2. It is scarcely probable that, as suggested by Bodroux, the fluorescent oil now shown to consist of dinaphthylmethane is a decomposition product resulting from distillation under diminished pressure; it is more probable that this hydrocarbon was not detected amongst the products of distillation under ordinary View Article Online 1144 HOMER : THE FRIEDEL-CRAFTS’ pressure because of its decomposition at the high temperature necessary for its distillation. Fraction iii (above 300°/20 mm.) was a deep red, viscous oil which deposited crystals. After purification these were obtained as a canary-yellow substance, melting at 252O, and giving an orange-coloured picrate. The quantity of this compound isolated was too small for analysis; it is possibly the s-88-dinaphthyl- ethane, Cl,H7*CH,*CH2*Cl,Hi, melting at 253*, prepared by Bamberger and Lodter (Ber., 1888, 21, 55). Thus the general result obtained is that the condensation products formed between as-dichloroethane and naphthalene, on dis- tillation under atmospheric pressure, give the methylnaphthalenes and PP-dinaphthyl, as stated by Bodroux ; whilst, on distillation under diminished pressure, dinaphthylmethane and a small pro- portion of a substance melting at 252O are obtained, but prac- tically no methylnaphthalenes or PP-dinaphthyl. (b) Imteraction of Nethylene Cliloride aqd Nap?bthalene. Bodroux (loc. cit.) was unable to isolate substances other than a- and P-methyl- and ethyl-naphthalenes and j3P-dinaphthyl. In the present investigation the only crystalline substances obtained from the distillation of the products under diminished pressure were naphthalene and PB-dinaphthyl, the latter identified by its melting point and the properties of its picrate. The failure to isolate dinaphthylmethane, CH2(C,,€17)2, was probably due to the fact that the reaction had to be initiated at a temperature favourable to the preponderat.ing effect of reaction (ii). (c) Interuction of Et7Lylene Bromide or Chloride and Published on 01 January 1910. Downloaded by Middle East Technical University (Orta Dogu Teknik U) 12/02/2016 20:08:00. Naphthalene. Silva (Bubl. SOC.chim., 1881, [ii], 36, 24) was unable to isolate substances other than a- and P-methyl- and ethyl-naphthalenes and PP-dinaphthyl.
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