MERCURY(II) SULFATE 1
HO
Mercury(II) Sulfate
HgSO4, H2SO4
(2)
OH
OH O
H2O
HO
HgSO4 OH
95%
[7783-35-9] HgO4S (MW 296.66)
Similarly to other mercury(II) salts, HgSO4 effects hydroly-
InChI = 1/Hg.H2O4S/c;1-5(2,3)4/h;(H2,1,2,3,4)/q+2;/p-
sis of vinyl halides to ketones9 and allylic oxidation (DeigŁs
2/fHg.O4S/qm;-2
reaction).10
InChIKey = DOBUSJIVSSJEDA-KQKOKJCMCA
Related Reagents. Mercury(II) Acetate.
(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.
1. (a) Larock, R. C., Angew. Chem., Int. Ed. Engl. 1978, 17, 27. (b) Larock,
Solubility: insol H2O (dec into a yellow, basic sulfate); sol HCl,
R. C., Tetrahedron 1982, 38, 1713. (c) Larock, R. C. Organomercury
hot dil H2SO4, HNO3, and conc solution of NaCl.
Compounds in Organic Synthesis; Springer: Berlin, 1985. (d) Larock,
Form Supplied in: white, odorless, monoclinic crystals, granules,
R. C. Solvomercuration/Demercuration Reactions in Organic Synthesis;
or powder.
Springer: Berlin, 1986.
Handling, Storage, and Precautions: acute poison; exposure to
2. Reicherst, J. S.; Nieuwland, J. A., Org. Synth., Coll. Vol. 1941, 1,
all mercury compounds is to be strictly avoided. Releases toxic
229.
Hg fumes when heated to decomposition. Protect from light.
3. (a) Mondon, A., Justus Liebigs Ann. Chem. 1954, 585, 43. (b) Fraser, M.
M.; Raphael, R. A., J. Chem. Soc 1952, 226.
4. Hajos, Z. G.; Doebel, K. J.; Goldberg, M. W., J. Org. Chem. 1964, 29,
2527.
In combination with strong acids1 4 or Dowex 50,4,5 HgSO4
5. (a) Newman, M. S., J. Am. Chem. Soc. 1953, 75, 4740. (b) Billimoria, J.
is often employed as a catalyst for effecting hydration of alkynes,
D.; MacLagan, N. F., J. Chem. Soc 1954, 3257.
which results in the formation of the corresponding ketones
6. Bucourt, R.; Tessier, J.; Nomin�, G., Bull. Soc. Chem. Fr., Part 2 1963,
(eq 1). This strategy has been used in the synthesis of 19-norpro-
1923.
gesterone6 and histamine.3b
7. Hauser, F. M.; Ellenberger, S. R.; Ellenberger, W. P., Tetrahedron Lett.
1988, 29, 4939.
O
HO
HO 8. Gonzalez, F.; Lesage, S.; Perlin, A. S., Carbohydr. Res. 1975, 42,
1% HgSO4
267.
Dowex 50
(1)
9. Arzoumanian, H.; Metzger, J., J. Organomet. Chem. 1973, 57, C1.
MeOH, H2O
84% 10. For a review, see: Arzoumanian, H.; Metzger, J., Synthesis 1971,
527.
D-Glucal has been found to produce (2R)-(1,2-dihydroxyethyl)-
�
furan when treated with HgSO4/H2SO4 (eq 2).7 Other glycals Pavel Kocovskż
undergo hydration or elimination.8 University of Leicester, Leicester, UK
Avoid Skin Contact with All Reagents