’H Nmr Spectra and Structure of a Unique Tetrachloropentacyclododecanone Derived from Monodechloroaldrin and Monodechloroisodrin

  • K. Mackenzie
  • C. H. M. Adams
  • D. J. Cawley
Part of the Environmental Science Research book series (ESRH, volume 4)


Some time ago we found1 that the hexachlorocyclodiene pesticides aldrin (1) isodrin (2) dieldrin (3) and endrin (4) (and several related compounds) were stereo-selectively monodehalogenated at the dichloromethylene bridge by heating with the elementary reagent Na(K)OR-DMSO (with or without added ROH) giving e.g. from aldrin and isodrin the pentachloro compounds (5), (6). The dienes (5) and (6) behave as expected when treated with acetic-sulphuric acid mixtures, dechloroaldrin giving almost entirely unrearranged acetate (7) and ca. 1% of a tetrachlorocarbonyl compound (√max 1785 vs cm.-1 m/e 310) whilst dechloroisodrin, charatteristically, gives predominantly the half-cage acetate (8).


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    C.H.M. Adams and K. Mackenzie, J. Chem. Soc., 1969, 480.Google Scholar
  2. 2.
    S.B. Soloway, A.M. Damiana, J.W. Sims, R. Bluestone and R.E. Lidov, J. Amer. Chem. Soc., 1960, 82, 5377.CrossRefGoogle Scholar
  3. 3.
    C.W. Bird, R.C. Cookson and E. Crundwell, J. Chem. Soc., 1961, 4809.Google Scholar
  4. 4.
    L. deVries and S. Winstein, J. Amer. Chem. Soc., 1960, 82, 5363.CrossRefGoogle Scholar
  5. 5.
    K. Mackenzie, J. Chem. Soc., 1962, 457.Google Scholar
  6. 6.
    S. Winstein, P. Carter, F.A.L. Anet and A.J.R. Bourn, J. Amer. Chem. Soc., 1965, 87, 5247.CrossRefGoogle Scholar
  7. 7.
    Full details of this and other work described here may be found in K. Mackenzie, C.R.M. Adams and D.J. Cawley, J. Chern. Soc. Perkin II, 1973 (in press).Google Scholar
  8. 8.
    A.A. Bothner-By and S.M. Castellano in Computer Programmes for Chemistry, (Editor D.F. Detar), Benjamin, 1968. K. Wiberg, Computer Programmes for Chemists, Benjamin, 1965.Google Scholar

Copyright information

© Springer Science+Business Media New York 1974

Authors and Affiliations

  • K. Mackenzie
    • 1
  • C. H. M. Adams
    • 1
  • D. J. Cawley
    • 1
  1. 1.School of ChemistryUniversity of BristolEngland

Personalised recommendations