6109nylsulfonyl)ethylene9 ( l l b ) (191 mg, 0.6 mmol) in xylene (5 mL) was heated under reflux for 30 min. The cooled solution was diluted with ether, and the white adduct 12b-15b (277 mg, 92.5%) was collected by filtration: 'H NMR (CDC13) 6 2.27 (m, 2 H), 3.68-4.05 (m, 2 H), 4.10 (m, 2 H), 4.90 (m, 2 H), 6.65 (m, 2 H), 7.00-8.05 (m, 18 H).Sodium Amalgam Reduction of Adducts 12b-15b. A mixture of adducts 12b-15b (272 mg, 0.45 mmol) was taken up in dry tetrahydrofuran (5 mL) and methanol (10 mL), containing sodium dihydrogen phosphate (1.2 g), and purged with nitrogen. With efficient stirring, 3% sodium amalgam (ca. 2.5 g) was added in small portions. After 16 h, the mixture was filtered through a Celite pad and poured onto brine (20 mL). The solvent was evaporated off on the rotary evaporator, and the aqueous residues were extracted with dichloromethane (4 X 20 mL). The combined organic layer was washed with water (2 X 20 mL) and brine (20 mL), dried (Na2S04), and evaporated to give 16-19 as a light yellow solid (140 mg, 97.8%). GC-MS analysis of this mixture showed it to be an isomeric mixture of four components, in the approximate ratio of 2:1:2:7 (column used: 12 m X 0.32 mm (i.d.), packed with fused silica-BPI type, column temperature 250 OC, isothermal conditions), all with the m / e (M+) of 318: IR (film, NaCl plate) 3054,
