The synthesis of thionaphthen derivatives from styrenes and thionyl chloride / by George Barger and Arthur James Ewins.

  • Barger, George, 1878-1939
Date:
[1908?]
Catalogue details

Licence: Public Domain Mark

Credit: The synthesis of thionaphthen derivatives from styrenes and thionyl chloride / by George Barger and Arthur James Ewins. Source: Wellcome Collection.

    7/12 (page 2090)
    thus again illustrating the greater reactivity of the bromo-compound as compared with the chloro-compound. Dichlcrocarbonyldioxymethylthionaphthen was obtained by heating 3 grams of rsosafrole dibromide with 13 grams of thionyl chloride to 220° for seven hours. On opening the tube, a few crystals were found to have separated, and, after cooling to -80°, 0*15 gram was collected. On recrystallisation from light petroleum (b. p. 70—100°), the substance melted at 180° : 0*1012 gave 0-1049 AgCl and 0-0879 BaS04. Cl = 25*6; S = 11*9. C10H4O3Cl2S requires 01 = 25*8; S = 11 *6 per cent. The constitution is doubtful, but the methyl group is most probably in position 1. In addition to the above, a substance was obtained, which crystallised from light petroleum, melted at 167°, and did not contain sulphur : 0-1288 gave 0-1793 CO, and 0-0115 H.,0. C = 37‘9; H=1*0. 0-1689 „ 0-3097 AgCl. Cl = 45*3. C10H4O3Cl4 requires C = 38f2 ; H= 1-2 ; Cl = 45-2 per cent. This substance is most probably represented by the formula oo<q>cshci2-cci:cci-ch3. The Wellcome Physiological Research Laboratories, Brockwell Hall, Herne Hill, London, .E. * R, LAY AND SONS, LTD., BREAD ST. HILL, F.P., AND BUNGAY, SUFFOLK