COPE elimination reaction observed in the biodegradation of quaternary ammonium surfactants

Abstract

The biodegradation of dialkyldimethylammonium compounds in aqueous solutions indicates that part of the degradation pathway includes the Cope elimination reaction, which does not occur under mild conditions in the absence of microorganisms.

References

1. J. Higgins, D. Scott and R. G. Hammond, in Microbial Degradation of Organic Compounds, ed. D. T. Gibson, Marcel Dekker, New York, 1984, pp. 43–87; D. Hampton and L. J. Zatman, J. Biochem. Soc. Trans., 1983, 1, 667; J. Colby and L. J. Zatman, Biochem. J., 1973, 132, 101; P. J. Larje, C. A. Boulton and M. G. C. Crabbe, Biochem. J., 1972, 128, 1879.
2. P. J. Larje, FEBS Lett., 1971, 18, 297; J. Colby and L. J. Zatman, Biochem. J., 1975, 148, 513; L. E. Zajic, B. Volesky and A. Wellman, Can. J. Microbiol., 1985, 15, 122; C. A. Boulton, J. C. Crabbe and P. J. Larje, Biochem. J., 1974, 140, 253.
3. A. C. Cope and E. R. Trumbull, Org. React., 1960, 11, 317; A. C. Cope, N. A. Le Bel and W. R. Moore, J. Am. Chem. Soc., 1961, 83, 3861; A. C. Cope and N. A. Le Bel, J. Am. Chem. Soc., 1960, 82, 4656; A. C. Cope, E. Ciganek, C. F. Howell and E. E. Schwerter, J. Am. Chem. Soc., 1960, 82, 4663.
4. H. H. Paradies, J. Phys. Chem., 1986, 90, 5956; H. H. Paradies, Medicinale, 1984, 14, 1.
5. S. F. Clancy, P. H. Steiger, D. A. Tanner, M. Thies and H. H. Paradies, J. Phys. Chem., 1994, 98, 11 143.
6. M. Thies, S. F. Clancy and H. H. Paradies, J. Phys. Chem., 1996, 100, 9881.