retention times of 155, 270, and 195 s for compounds 1-3, respectively. The trans (2) to cis (3) ratio is about 11:1. In a typical reaction, a 50-cm1 23 round-bottomed flask with a side arm for sampling was charged with 243 mg (0.755 mmol) tetrabutylammonium bromide and with a 15.1 mmol allylbenzene in 8.00 cm3 of toluene solution (1.42 M at 75 °C). The mixture was heated to 75 °C and 5.00 mL of aqueous 50% NaOH preheated to 75 °C was added, stirring was commenced, and the time was taken. At regular intervals, 5.0-mL samples of the upper organic layer were taken and immediately injected into the gas chromatograph. Phase separation was almost immediate after stopping the stirring. No less than nine samples were taken per run. The temperature was maintained ±0.4 °C by a Fried thermoregulator, electric relay, and thermostated bath. Stirring was provided by a Heidolph mechanical stirrer with appropriate gears attached to a flat-bladed Teflon paddle. The stirring speed was determined by a Jaquet tachometer to ±10 rpm.
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