Summary
In nitromethane, the methanolysis of aryl acetates is catalysed by the tetrafluoroborate and hexafluorophosphate salts of the (η 5-ethyltetramethylcyclopentadienyl) (η 6-benzen)rhodium(III) cation. Under the conditions of the methanolysis, the anion of the latter salt reacts with methanol to give dimethyl phosphorofluoridate. The hydrogen fluoride formed also in this reaction is thought to be responsible for the greater efficiency of the hexafluorophosphate salt as a catalyst for the methanolysis.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
A. Wu, E. R. Biehl and P. C. Reeves,J. Chem. Soc., Perkin Trans.,2, 449 (1972).
F. G. Bordwell and G. D. Cooper,J. Amer. Chem. Soc.,74, 1058 (1952).
S. G. Davies,Organotransition Metal Chemistry-Applications to Organic Synthesis, Pergamon Press, Oxford, 1982. For specific examples see: J. Blagg and S. G. Davies,J. Chem. Soc., Chem. Commun, 492 (1986); S. J. Coote and S. G. Davies,J. Chem. Soc., Chem. Commun., 648 (1988); G. Jaouen, S. Top, A. Laconi and D. Couturier,J. Amer. Chem. Soc.,106, 2207 (1984).
P. M. Triechel and L. D. Rosenheim,Inorg. Chem.,20, 942 (1981).
C. White, S. J. Thompson and P. M. Maitlis,J. Organomet. Chem. 127, 415 (1977).
C. White, S. J. Thompson and P. M. Maitlis,J. Chem. Soc., Dalton Trans., 1654 (1977).
N. A. Bailey, E. H. Blunt, G. Fairhurst and C. White,J. Chem. Soc., Dalton Trans., 829 (1980).
Dictionary of Organic Compounds, 5th Edn, Chapman and Hall, London, 1982.
R. P. Houghton, M. Voyle and R. Price,J Chem. Soc., Perkin Trans. I, 925 (1984).
T. Nishioka, T. Fujita, K. Kitamura and M. Nakajima,J. Org. Chem. 40, 2520 (1975).
L. A. Cohen and S. Takehashi,J. Amer. Chem. Soc.,95, 443 (1973).
P. M. Treichel and G. Werber,Inorg. Chem.,4, 1098 (1965).
J. F. Nixon and R. Schmutzler,Spectrochim. Acta 20, 1835 (1964).
W. J. Stec, J. R. Van Wazer and N. Goddard,J. Chem. Soc., Perkin Trans.,2, 463 (1972).
G. S. Reddy and R. Schmutzler,A. Naturforsch., B.,25, 1199 (1970).
P. P. Mager,Pharmazie,36, 511 (1981).
F. L. Wimmer and M. R. Snow,Aust. J. Chem.,31, 267 (1978).
G. Fairhurst and C. White,J. Chem. Soc., Dalton Trans., 1524 (1979).
S. J. Thompson, P. M. Bailey, C. White and P. M. Maitlis,Angew. Chem. Int. Edn Engl.,15, 490 (1976).
C. White, S. J. Thompson and P. M. Maitlis,J. Organometal. Chem. 134, 319 (1977).
J. W. Kang and P. M. Maitlis,J. Organometal. Chem. 30, 127 (1971).
A. Nutton, P. M. Bailey and P. M. Maitlis,J. Chem. Soc., Dalton Trans., 1997 (1981).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Dunlop, J.E., Houghton, R.P. The rhodium-catalysed methanolysis of aryl acetates and of the hexafluorophosphate anion. Transition Met Chem 15, 48–50 (1990). https://doi.org/10.1007/BF01032231
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01032231