ozone; ethenetetracarbonitrile in ethyl acetate T=-78°C; 0.5 h;

lead(IV) acetate in pyridine 1.5 h;

sodium periodate in tetrahydrofuran; water 2 h;

1: 78 percent / Li(t-BuO)3AlH / tetrahydrofuran / 3 h / Ambient temperature 3: 73 percent / 5 h / 220 °C 4: 87 percent / hydrazine hydrate / ethanol; bis-(2-hydroxy-ethyl) ether / 72 h / Heating 5: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h 6: 83 percent / petroleum ether / 3 h / 0 °C 7: 79 percent / 0.5 h / 140 °C 8: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 9: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

1: 87 percent / hydrazine hydrate / ethanol; bis-(2-hydroxy-ethyl) ether / 72 h / Heating 2: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h 3: 83 percent / petroleum ether / 3 h / 0 °C 4: 79 percent / 0.5 h / 140 °C 5: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 6: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

2: 73 percent / 5 h / 220 °C 3: 87 percent / hydrazine hydrate / ethanol; bis-(2-hydroxy-ethyl) ether / 72 h / Heating 4: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h 5: 83 percent / petroleum ether / 3 h / 0 °C 6: 79 percent / 0.5 h / 140 °C 7: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 8: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

1: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h 2: 83 percent / petroleum ether / 3 h / 0 °C 3: 79 percent / 0.5 h / 140 °C 4: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 5: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

1: 73 percent / 5 h / 220 °C 2: 87 percent / hydrazine hydrate / ethanol; bis-(2-hydroxy-ethyl) ether / 72 h / Heating 3: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h 4: 83 percent / petroleum ether / 3 h / 0 °C 5: 79 percent / 0.5 h / 140 °C 6: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 7: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

1: 83 percent / petroleum ether / 3 h / 0 °C 2: 79 percent / 0.5 h / 140 °C 3: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 4: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme

1: 79 percent / 0.5 h / 140 °C 2: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C) 3: 57 percent / tetracyanoethylene, ozone / ethyl acetate / 0.5 h / -78 °C View Scheme