dimethylsulfide; ozone 1) MeOH, CH2Cl2, -78 deg C, 2) to RT; Yield given. Multistep reaction;

1: 40 percent / TiCl4, Ti(O(i)Pr)4 / CH2Cl2 / 1 h / -78 °C 2: 86 percent / tetrahydrofuran / 48 h / Ambient temperature 3: 77 percent / 2N HCl / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: chloro-trimethyl-silane; 3-methyl-cyclohex-2-en-1-one With copper(l) iodide; lithium chloride in tetrahydrofuran T=-40°C; 0.166667 h; Inert atmosphere; 2: methyl-magnesium chloride in tetrahydrofuran T=-40°C; 0.75 h; 3: With water; ammonium chloride in tetrahydrofuran

copper(l) iodide; lithium chloride in tetrahydrofuran T=0°C; 0.5 h;

1: 3-methyl-cyclohex-2-en-1-one; methyllithium With copper(l) iodide T=-10°C; 2: chloro-trimethyl-silane With N,N,N',N',N'',N''-hexamethylphosphoric triamide; triethylamine T=-10 - 20°C; 15 h;

1: 3-methyl-cyclohex-2-en-1-one; methyl cuprate in tetrahydrofuran T=-40°C; 0.666667 h; 2: chloro-trimethyl-silane in tetrahydrofuran T=-40 - 22°C; 4 h; Further stages.;

in acetonitrile Irradiation; Yields of byproduct given;

triethylamine Multistep reaction;