Mercury(II) Sulfate


[7783-35-9]  · HgO4S  · Mercury(II) Sulfate  · (MW 296.66)

(converts alkynes and vinyl halides into ketones;1-5,9 facilitates conversion of glucals into furan derivatives7)

Alternate Name: mercuric sulfate.

Physical Data: mp dec; d 6.470 or 7.56 g cm-3.

Solubility: insol H2O (dec into a yellow, basic sulfate); sol HCl, hot dil H2SO4, HNO3, and conc solution of NaCl.

Form Supplied in: white, odorless, monoclinic crystals, granules, or powder.

Handling, Storage, and Precautions: acute poison; exposure to all mercury compounds is to be strictly avoided. Releases toxic Hg fumes when heated to decomposition. Protect from light.

In combination with strong acids1-4 or Dowex 50,4,5 HgSO4 is often employed as a catalyst for effecting hydration of alkynes, which results in the formation of the corresponding ketones (eq 1). This strategy has been used in the synthesis of 19-norprogesterone6 and histamine.3b

D-Glucal has been found to produce (2R)-(1,2-dihydroxyethyl)furan when treated with HgSO4/H2SO4 (eq 2).7 Other glycals undergo hydration or elimination.8

Similarly to other mercury(II) salts, HgSO4 effects hydrolysis of vinyl halides to ketones9 and allylic oxidation (Deigès reaction).10

Related Reagents.

Mercury(II) Acetate.

1. (a) Larock, R. C. AG(E) 1978, 17, 27. (b) Larock, R. C. T 1982, 38, 1713. (c) Larock, R. C. Organomercury Compounds in Organic Synthesis; Springer: Berlin, 1985. (d) Larock, R. C. Solvomercuration/Demercuration Reactions in Organic Synthesis; Springer: Berlin, 1986.
2. Reicherst, J. S.; Nieuwland, J. A. OSC 1941, 1, 229.
3. (a) Mondon, A. LA 1954, 585, 43. (b) Fraser, M. M.; Raphael, R. A. JCS 1952, 226.
4. Hajos, Z. G.; Doebel, K. J.; Goldberg, M. W. JOC 1964, 29, 2527.
5. (a) Newman, M. S. JACS 1953, 75, 4740. (b) Billimoria, J. D.; MacLagan, N. F. JCS 1954, 3257.
6. Bucourt, R.; Tessier, J.; Nominé, G. BSF(2) 1963, 1923.
7. Hauser, F. M.; Ellenberger, S. R.; Ellenberger, W. P. TL 1988, 29, 4939.
8. Gonzalez, F.; Lesage, S.; Perlin, A. S. Carbohydr. Res. 1975, 42, 267.
9. Arzoumanian, H.; Metzger, J. JOM 1973, 57, C1.
10. For a review, see: Arzoumanian, H.; Metzger, J. S 1971, 527.

Pavel Ko&cbreve;ovský

University of Leicester, UK

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