7184 Table 1. Reaction of Phenvlhvdrosvlamine with Benzene
An Acid-Catalyzed Reaction of Arylhydroxylamines with Benzene. Selectivity of the Reaction Sites Sir: W e have previously described the reaction of arylhydroxylamines with benzene catalyzed by trifluoroacetic acid (TFA) which yields diphenylamines.' In this communication we wish to report the reaction of arylhydroxylamines with benzenes in which a carbon-carbon bond between the two aromatic rings is formed.
Run 1 2 3 4 5 6 7 8 9 10
_
Amounts of acid5 (mol)" CF,CF,CO,H SO,H 4 10 25 25 25 25 25 0 0 _ 0
_
0 0 0 0 0.2 1.2 2.3 2.0 4.0 20.0~
Benzene (moW
Procedure
3.5 9.0 22.0 22.0 22.5 22.5 22.5 60.0 60.0 60.0
c, P , g c, e , g c, e , g
c, e c, e c, f c,
f
d, f d, f __ d, f
Product (%)* ____ 2
3a
4a
41 56 46 12 20 39 14 2 1
