FLUORINATED ARYL NITRENE PRECURSORS - Nitrenes and Nitrenium Ions - page 464

TABLE 11.2. Products Formed in the Oxidation of Fluoroanilines 38

Yield (%)

Fluoroaniline Fluoroazobenzene Fluorophenazine

1a : 2F 52 Trace

2b : 3F 50 None

1c : 4F 94 None

1d : 2,4F 52 24

1e : 2,5F 62 Trace

1f : 2,6F 65 25

1g : 3,4F 60 None

1h : Pentafluoro 60 25

nucleophile not only on nitrogen but also on the ortho position of the aromatic ring.
Nucleophilic attack by remaining fluoroaniline on nitrogen would give fluorohy-
drazobenzene, which would oxidize to form fluoroazobenzene. On the other hand,
the electron-deficient

1 FPhN could be attacked at

the ortho position by the

SCHEME 11.15.