Mercury(II) Pivalate


[32276-77-0]  · C10H18HgO4  · Mercury(II) Pivalate  · (MW 402.87)


Alternate Name: mercuric pivalate.

Solubility: sol THF, DME; insol benzene, hexane, etc.

Preparative Methods: see White et al.2

Handling, Storage, and Precautions: acute poison; mercury carboxylates are generally easily absorbed through the skin and are corrosive; exposure to all mercury compounds is to be strictly avoided. Releases toxic Hg fumes when heated to decomposition. Protect from light.

Mercury(II) pivalate has similar synthetic applications as the acetate and other HgII electrophiles.1,2 In contrast to, e.g. Mercury(II) Acetate, the pivalate has better solubility in THF and exhibits higher regio- and stereoselectivity in oxymercuration reactions.3 The pivalate has been employed to conduct the intramolecular oxymercuration which afforded isolineatin in 42% yield after hydride reduction of the intermediate organomercurial (eq 1).2

Related Reagents.

Mercury(II) Acetate; Mercury(II) Trifluoroacetate.

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. White, J. D.; Avery, M. A.; Carter, J. P. JACS 1982, 104, 5486.
3. Sheldon, B. G. Ph.D. Thesis, Oregon State University, 1981.

Pavel Ko&cbreve;ovský

University of Leicester, UK

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.