mL of benzene was added 0.40 mL of a 0.1 M solution of potassium tert-butoxide in tert-butyl alcohol. The mixture was stirred for 5 min at room temperature, diluted with ether, washed with saturated aqueous ammonium chloride, water, and brine, dried, and concentrated in vacuo to give 26 mg of a yellow solid. The material was subjected to preparative high-pressure LC using a 50 cm X 0.8 cm column packed with -20-µ porous silica beads.44 Elution with 35% ether in hexane at a flow rate of 4.8 mL/min gave two bands: band 1, retention time 11 min, 13 mg (48%) of 4-cyano-6,6-diphenylbicyclo[3.1.0]hex-3-en-2-one as faint yellow microcrystals, mp 178-179 °C; band 2, retention time 15 min, 11 mg (45%) of starting monobromo ketone. No 1-cyano-4-bromo-6,6-diphenylbicyclo [3.1.0] hexan-3-one (retention time 21 min) was observed.Control Experiment. Treatment of l-Cyano-6,6-diphenylbicyclo[3.1.0]hexan-3-one with Potassium tert-Butoxide. To a solution of 18 mg (0.066 mmol) of the 3-oxobicyclic compound in 4 mL of tert-butyl alcohol and 1 mL of benzene was added 0.66 mL of a 0.1 M solution of potassium tert-butoxide in tert-butyl alcohol. The mixture was stirred for 5 min at room temperature, diluted with ether, washed with saturated aqueous ammonium chloride, water, and brine, dried, and concentrated in vacuo to give 18 mg of a colorless oil. NMR analysis indicated pure starting ketone.Control Experiment. Treatment of 5-Cyano-6,6-diphenylbicyclo[3.1.0]hex-3-en-2-one with Potassium tert-Butoxide. To a solution of 27 mg (0.1 mmol) of the 5-cyano enone in 4.0 mL of tert-butyl alcohol and 1.0 mL of benzene was added 1.0 mL of a 0.1 M solution of potassium tert-butoxide in tert-butyl alcohol. The mixture was stirred for 5 min at room temperature, diluted with ether, washed with saturated aqueous ammonium chloride, water, and brine, dried, and concentrated in vacuo to give 27 mg of a white solid. NMR analysis indicated pure starting enone.Emission Measurements. Phosphorescence measurements were made on an Aminco-Kiers spectrophosphorimeter equipped with a Hanovia 901C-1,150-W, xenon arc lamp and modified with internal baffles to eliminate scatter. The spectra were obtained at 77 K in ethanol-ether (2:1) with the samples being thoroughly degassed immediately before measurements were made. The emission spectra were calibrated by use of a low-pressure mercury lamp in each run.