Aromatic fluorine compounds. VI. Displacement of aryl fluorine in diazonium salts
Journal of the American Chemical Society
By: G. C. Finger and R.E. Oesterling
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Abstract
Several chlorofluorobenzenes have been isolated from the Schiemann synthesis of fluorobenzenes. These have been shown to be the products of two side reactions occurring during thermal decomposition of the dry benzenediazonium fluoborate salt containing coprecipitated sodium chloride, an unavoidable contaminant in large preparations involving the use of hydrochloric acid and sodium fluoborate. The major side reaction and its chloro product were unexpected; a unique displacement of fluorine ortho to the diazonium group was observed. Replacement of the diazo group with chlorine was the predicted side reaction which proved to be minor. Conditions causing the side reactions and the isolation and identification of the products are described.
| Publication type | Article |
|---|---|
| Publication Subtype | Journal Article |
| Title | Aromatic fluorine compounds. VI. Displacement of aryl fluorine in diazonium salts |
| Series title | Journal of the American Chemical Society |
| Volume | 78 |
| Issue | 11 |
| Year Published | 1956 |
| Language | English |
| Larger Work Type | Article |
| Larger Work Subtype | Journal Article |
| Larger Work Title | Journal of the American Chemical Society |
| First page | 2593 |
| Last page | 2596 |
| Google Analytic Metrics | Metrics page |