Summary
-
1.
It was shown that 3, 3, 3-trifluoropropene, trifluoroethylene, and 1,1-diflnoroethylene readily undergo addition of bromine in glacial acetic acid.
-
2.
For the first time, fluoroolefins were caused to undergo conjugated addition. By the action of bromine on some fluoroolefins in glacial acetic acid, some acetic esters of β -bromo α,α -difluoro alcohols were prepared.
-
3.
It was shown that compounds of this new type have the character of mixed acid anhydrides.
-
4.
By conjugated addition of bromine in water, the bromohydrin of 3,3,3-trifluoropropene was obtained, and this was converted into 2,3-epoxy- 1,1,1-trifluoropropane.
-
5.
By conjugated addition of bromine to trifluoroethylene in water, bromofluoroacetic acid was obtained.
-
6.
The addition of mercuric acetate to 1,1-difluoroethylene was effected in acetic acid and in alcohol, the products being the unstable 2-acetoxy-2,2-difluoroethylmercury and 2-ethoxy-2,2-difluoroethylmercury acetates, which are readily transformed into a (halomercuri)acetic acid and its esters.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
M. Hauptshein, C. Stokes and A. Grosse, J. Am. Chem. Soc. 74, No. 8, 1974 (1952).
R. Haszeldine, J. Chem. Soc. 1952, 4260.
J. Dickey and E. Towne, US Patent 2700686 (1955).
E. McBee and T. Burton, J. Am. Chem. Soc. 74, No. 2, 3022 (1952).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Knunyants, I.L., Pervova, E.Y. & Tyuleneva, V.V. Addition reactions of perfluoroolefins communication 5. Conjugated addition of halogens. Russ Chem Bull 5, 863–869 (1956). https://doi.org/10.1007/BF01169991
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01169991