dipyridinium dichromate in dichloromethane T=20°C; 4 h; Inert atmosphere;

4-methylmorpholine N-oxide in acetonitrile T=0 - 20°C; Inert atmosphereMolecular sieve;

1: With diisobutylaluminium hydride in dichloromethane T=0 - 20°C; 2 h; 2: With hydrogenchloride; water in dichloromethane T=0°C;

1: With diisobutylaluminium hydride in tetrahydrofuran T=20°C; 0.75 h; Inert atmosphereCooling with ice; 2: With pyridinium chlorochromate in dichloromethane T=20°C;

1.1: sulfuric acid / Reflux; Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

1.1: hydrogenchloride; sodium hydroxide; sodium nitrite / water / 2 h / 0 °C / Inert atmosphere 1.2: 0.83 h / 35 - 90 °C / Inert atmosphere 2.1: sulfuric acid / Reflux; Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0 - 20 °C / Inert atmosphere 3.2: 0 °C / Inert atmosphere 4.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

1.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0 - 20 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

1.1: bromine; acetic acid / 16 °C / Inert atmosphere 2.1: hydrogenchloride; sodium hydroxide; sodium nitrite / water / 2 h / 0 °C / Inert atmosphere 2.2: 0.83 h / 35 - 90 °C / Inert atmosphere 3.1: sulfuric acid / Reflux; Inert atmosphere 4.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 0 - 20 °C / Inert atmosphere 4.2: 0 °C / Inert atmosphere 5.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

1: N-bromosuccinmide; dibenzoyl peroxide / 1,2-dichloro-ethane / 5 h / Inert atmosphere; Reflux; Irradiation 2: 4-methylmorpholine N-oxide / acetonitrile / 0 - 20 °C / Inert atmosphere; Molecular sieve View Scheme

cesium fluoride; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) in toluene; acetonitrile T=110°C; 12 h;