5,5-Dibromo-2,2-dimethyl-1,3-dioxane-4,6-dione

Reactions

Selective α-bromination of aldehydes and α′-bromination of α,β-unsaturated ketones; reductive coupling to an ethylenetetracarboxylate.

Synthesis

The preparative method of 5,5-Dibromo-2,2-dimethyl-1,3-dioxane-4,6-dione: by bromination of Meldrum's acid (2,2-Dimethyl-1,3-dioxane-4,6-dione) (commercially available) with Bromine in the presence of Potassium Hydroxide or Sodium Hydroxide eq 1).

References

1. Bloch, R. S 1978, 140.
2. Davidson, D.; Bernhard, S. A. JACS 1948, 70, 3426.
3. Synder, H. R.; Kruse, C. W. JACS 1958, 80, 1942.
4. Novikov, V. L.; Shestak, O. P.; Kamernitskii, A. V.; Elyakov, G. B. Izv. Akad. Nauk SSSR, Ser. Khim. 1982, 476 (CA 1982, 96, 180 832).