1: 1-Methyl-1-(cyclopropylethinyl)-cyclopropan With N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium in hexane; pentane T=20°C; 2 h; 2: dimethyl sulfate in hexane; pentane T=20°C; 1 h;

1.1: nBuLi / diethyl ether; hexane / 16 h / 20 °C 1.2: 86 percent / diethyl ether; hexane / 1 h / 20 °C 2.1: N,N,N',N'-tetramethylethylenediamine; tBuLi / hexane; pentane / 2 h / 20 °C 2.2: 84 percent / hexane; pentane / 1 h / 20 °C View Scheme

1: <PhCH2NEt3>Cl, aq. NaOH 2: Li / 2-methyl-propan-2-ol View Scheme

1: TsOH 2: <PhCH2NEt3>Cl, aq. NaOH 3: Li / 2-methyl-propan-2-ol View Scheme

lithium in tert-butyl alcohol

lithium in tert-butyl alcohol