zinc in tetrahydrofuran 4 h; Further byproducts given;

sodium sulfate; silver(l) oxide 1.) DMF, -23 deg C, 3 h, 2.) Et2O, reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

(NH4)2S2O8; silver nitrate

(i) BF3*Et2O, dioxane, (ii) Ag2O, Et2O; Multistep reaction;

(i) BF3-Et2O, dioxane, (ii) Ag2O, MgSO4, Et2O; Multistep reaction;

1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating 4.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 5.1: pyridine / 16 h / 20 °C 6.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C 7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 7.2: 57 percent / tetrahydrofuran; hexane / 2 h / -78 °C 8.1: 77 percent / AlCl3 / CH2Cl2 / 4 h / 20 °C View Scheme

(i) SnCl2, aq. HCl, dioxane, (ii) ZnCl2; Multistep reaction;

1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating 4.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 5.1: pyridine / 16 h / 20 °C 6.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C 7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 7.2: 8 percent / tetrahydrofuran; hexane / 2 h / -78 °C View Scheme