1: in tetrahydrofuran T=0 - 5°C; 0.333333 h; 2: With water; citric acid in tetrahydrofuran T=25°C;

in tetrahydrofuran; diethyl ether T=-78°C; 0.5 h; Yield given;

iron (III) acetylacetonate in tetrahydrofuran T=-78°C;

1: 97 percent / aq. KOH / dioxane / 1 h 2: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / 40 h / -18 °C 3: 0.16 g / Fe(acac)3 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / 40 h / -18 °C 2: 0.16 g / Fe(acac)3 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 77 percent / NaH / tetrahydrofuran 2: 98 percent / KOH / H2O; diethyl ether 3: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / -18 °C 4: [Fe(acac)3] / tetrahydrofuran / -78 - 0 °C View Scheme

1: 76 percent / K2CO3; NaI / dimethylformamide / 6 h / 20 °C 2: 97 percent / aq. KOH / dioxane / 1 h 3: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / 40 h / -18 °C 4: 0.16 g / Fe(acac)3 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

methyllithium -78 deg C to r.t.; Yield given;

1.1: TiCl4; (iPr)2NEt / CH2Cl2 / 2 h / 0 °C 1.2: 73 percent / CH2Cl2 / 3 h / -78 °C 2.1: 240 mg / aq. HCl / tetrahydrofuran / 14 h / 20 °C 3.1: 92 percent / camphor-10-sulfonic acid / 20 °C 4.1: pyridine / CH2Cl2 / 1 h / -20 °C 5.1: 74 percent / [15]crown-5 ether / tetrahydrofuran / 24 h / 20 °C 6.1: 51 percent / aq. cerium ammonium nitrate / acetonitrile / 1 h 7.1: pyridine / CH2Cl2 / 0.5 h / 0 °C 7.2: 81 percent / ethyl(diisopropyl)amine / DMAP / CH2Cl2 / 24 h 8.1: 70 percent / Mo[N-(tBu)(3,5-dimethylphenyl)]3 / toluene / 20 h / 80 °C 9.1: 82 percent / hydrogen / Lindlar / CH2Cl2 / 5 h / 750.06 Torr 10.1: 62 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C 11.1: 80 percent / aq. acetic acid / 2 h / 60 °C View Scheme

1.1: TiCl4; (iPr)2NEt / CH2Cl2 / 2 h / 0 °C 1.2: 73 percent / CH2Cl2 / 3 h / -78 °C 2.1: 240 mg / aq. HCl / tetrahydrofuran / 14 h / 20 °C 3.1: 92 percent / camphor-10-sulfonic acid / 20 °C 4.1: pyridine / CH2Cl2 / 1 h / -20 °C 5.1: 45 mg / [15]crown-5 ether / tetrahydrofuran / 20 °C 6.1: 70 percent / Mo[N-(tBu)(3,5-dimethylphenyl)]3 / toluene / 20 h / 80 °C 7.1: 100 percent / hydrogen / Lindlar / CH2Cl2 8.1: 78 percent / aq. cerium ammonium nitrate / acetonitrile / 3 h View Scheme