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In one case the intermediate N-tosylurethane was isolated by cooling and filtering the reaction mixture as soon as the addition of tosyl isocyanate had been completed. The solid was recrystallized from ether and melted at 132-133 °C. la,9a-Methylene-7/?-acetyl-10/3-methyldecalin (12). A sample of olefin 11 (1.0 g, 4.9 mmol) in 38 mL of methylene chloride and 9 mL of methanol was cooled in a dry ice-acetone bath and ozonized until a light blue solution was obtained. The excess ozone was flushed with a slow stream of nitrogen gas. Dimethyl sulfide (3 mL) was added dropwise to the colorless solution. The reaction solution was allowed to warm and stirred at room temperature overnight. Then it was washed with water (2 X 50 mL) and dried over MgS04, and the solvent was removed under reduced pressure. The residue was passed through a short column (60 g of Si02), using 1:2 methylene chloride/hexane as the eluant, to afford 12 as a colorless liquid (0.93 g, 4.5 mmol, 92%), bp 90 °C (0.1 mmHg). The structure was assigned on the basis of spectral properties: IR (neat) 1700 (C=0) cm'1; NMR (CDC13) 0.00-0.90 (m, 3 H, cyclopropyl) 1.10 (s, 3 H, angular CH3), 2.10 (s, 3 H, COCH3), 0.90-3.00 (m, 13 H, ring protons).

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