1: methyl acetophenone-4-carboxylate With trimethylsilyl trifluoromethanesulfonate; diethylphosphinoethane in dichloromethane; toluene T=20°C; 1 h; Inert atmosphere; 2: methylmagnesium bromide in tetrahydrofuran; dichloromethane; toluene T=20°C; 0.25 h; Inert atmosphere; 3: With water; sodium hydrogencarbonate in tetrahydrofuran; methanol; dichloromethane; toluene T=40°C; 2 h; chemoselective reaction;

1: methyl acetophenone-4-carboxylate With O,N-dimethyl-hydroxylamine hydrochloride; diisobutylaluminium hydride in tetrahydrofuran T=0 - 20°C; Inert atmosphere; 2: With 4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde in tetrahydrofuran; diethyl ether T=0°C; 1 h; 3: methyllithium in tetrahydrofuran; diethyl ether T=-78°C; 1 h;

methanol; N,N,N',N',N'',N''-hexamethylphosphoric triamide; samarium diiodide in tetrahydrofuran T=25°C; Rearrangement; reduction;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; samarium diiodide in tetrahydrofuran T=25°C; Rearrangement; reduction;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; samarium diiodide in tetrahydrofuran Decomposition; Heating;

in cyclohexane T=250°C; 1 h;

2: 10percent HCl / acetone / Heating View Scheme

3,3-dimethyldioxirane in acetone T=25°C; 1.5 h; relative rate; Rate constant;

1: 2: With water

2: 72 h 3: diethyl ether / 0.5 h / 0 °C 4: toluene / 1 h / 100 °C 5: cyclohexane / 1 h / 250 °C View Scheme