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DOI: 10.15227/orgsyn.000.0019
m-THIOCRESOL1
WARNING
Diazonium xanthates (ArN=NSCSOC2Hs) can detonate, and this procedure should be followed carefully to ensure decomposition of the xanthate as it is formed. Under no circumstances should the diazonium solution and the potassium ethyl xanthate be mixed cold and the mixture subsequently heated. A severe detonation has been reported when such a procedure was employed during the preparation of thiocresol.
It has been observed2 that the dropwise addition of an aqueous solution of potassium ethyl xanthate to a cold (0°) aqueous solution of diazotized orthanilic acid results in the immediate loss of nitrogen when a trace of nickel ion is present in the stirred diazonium solution.3 The catalyst can be added as nickelous chloride or simply by using a nichrome wire stirrer. When no nickel ion is added and a glass stirrer is employed, the diazonium xanthate precipitates and requires heat (32°) to effect decomposition.
The use of a nichrome stirrer or a catalytic amount of nickel ion is recommended1 for such reactions to minimize the accumulation of diazonium xanthate; however, the catalytic role of nickel ion has not been explored with other diazonium salts.

References and Notes
  1. Org. Syntheses, Coll. Vol. 3, 809 (1955).
  2. William E. Parham and William R. Hasek, unpublished work.
  3. William R. Hasek, Ph.D. Thesis, The University of Minnesota, 1953, p. 121.