Grignard degradation

What is Grignard degradation?

The Grignard degradation technique involves the gradual removal of halogen atoms from a polyhalo compound using its corresponding Grignard reagent. Upon treatment with water, the resulting product contains one less halogen atom than the original compound.

This method of dehalogenation occurs in a stepwise manner, with each successive reaction resulting in the removal of one halogen atom from the molecule. The process continues until the desired level of dehalogenation has been achieved.

Grignard degradation
Grignard degradation

References

  • Steinkopf, W., Jacob, H. and Penz, H. (1934), Studien in der Thiophenreihe. XXVI. Isomere Bromthiophene und die Konstitution der Thiophendisulfonsäuren. [Studies in the thiophene series. XXVI Isomeric bromothiophenes and the constitution of thiophenedisulfonic acids.] Justus Liebigs Ann. Chem., 512: 136-164. https://doi.org/10.1002/jlac.19345120113
  • Steinkopf, W. and v. Petersdorff, H.-J. (1940), Studien in der Thiophenreihe. LI. Atophanartige Derivate des Dithienyls und Diphenyls. [Studies in the thiophene series. LI. Atophane-like derivatives of dithienyl and diphenyl.] Justus Liebigs Ann. Chem., 543: 119-128. https://doi.org/10.1002/jlac.19405430110
  • Grignard, V. “Sur quelques nouvelles combinaisons organométalliques du magnesium et leur application à des Synthèses d’alcools et d’hydrocarbures” [On some new organometallic combinations of magnesium and their application to the synthesis of alcohols and hydrocarbons] Comptes Rendus Hebdomadaires des Séances de L’Academie des Sciences 1900, 130, 1322-1324.
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