Table 3.

Oxidative chlorination of cyclooctene (16).

Entry	Oxidant	React. cond.a	Conv.b (%)
1	H2O2	TFEc, 2 h at r.t.	60
2	H2O2	2 h at 85°C	62
3	UHP	2 h at r.t.	5
4	UHP	2 h at 85°C	17
5	UHPd	2 h at r.t.	38
6	UHP	TFEc, 2 h at r.t.	84

^a Reaction conditions: 2.0 mmol (0.164 mL) of conc. HCl was added to 1.0 mmol (0.102 mL) of 30% aq. H₂O₂ or 1.0 mmol (94 mg) UHP, after quoted time 1.0 mmol (110 mg) of cyclooctene (16) was added and stirred for 2 h at room temperature. ^b Conversion of 16 by ¹H-NMR spectroscopy. ^c 1 mL of TFE. ^d 1.0 mmol (94 mg) of powdered UHP was heated for 30 min at 85 °C, after cooling 2.0 mmol (0.164 mL) of conc. HCl and 1.0 mmol (110 mg) of 16 were added.