thumbnail

Aromatic fluorine compounds. VI. Displacement of aryl fluorine in diazonium salts

Journal of the American Chemical Society

By:
and

Links

  • The Publications Warehouse does not have links to digital versions of this publication at this time
  • Download citation as: RIS

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.

Additional Publication Details

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