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Original Articles

Formation of Diphenyl Sulfoxide and Diphenyl Sulfide via the Aluminum Chloride–Facilitated Electrophilic Aromatic Substitution of Benzene with Thionyl Chloride, and a Novel Reduction of Sulfur (IV) to Sulfur (II)

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Pages 2535-2542 | Received 21 Jan 2010, Accepted 25 Feb 2010, Published online: 19 Nov 2010

REFERENCES

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  • “ The gas that evolved in such a reaction performed at 0°C with the molar ratio of PhH:SOCl2:AlCl3 = 2:1:1 was tested by a wet mixture of starch and potassium iodide (KI) ” . The color turned dark blue immediately, indicating formation of chlorine (Cl2) in the reaction .
  • DeHaan , F. P. , Ahn , P. Y. , Kemnitz , C. R. , Ma , S. K. , Na , J. , Patel , B. R. , Ruiz , R. M. and Villahermosa , R. M. 1998 . Int. J. Chem. Kinet. , 30 : 367
  • “ Purity of the Ph2SO product was determined by comparison of the Ph2SO peak area to the tiny impurity (Ph2S) peak area ” . No other impurities were found in GC-MS .
  • “ The molar ratio of Ph2S:Ph2SO in the isolated product (1.76 g) was determined to be 1.4:1 by comparison of the related GC peak areas ” . Ph2S (37%) and Ph2SO (27%), the percent yields based on the quantity of SOCl2, were determined according to the total quantity of the isolated product (1.76 g) and the Ph2S:Ph2SO molar ratio (1.4:1) in the product. By comparison of the PhSO2SPh GC peak area with that for Ph2SO, the yield of PhSO2SPh in this and all the other samples containing it was estimated to be about 5% .

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