ruthenium(II)-carbonyl-tris(triphenylphosphine) dihydride; Et3SiD; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in deuterated toluene T=125°C; 0.833333 h; Sealed NMR tubeInert atmosphere; Mechanism;

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere; |Cooling with ice 1.2: |Inert atmosphere; |Cooling with ice 2.1: potassium hydrogensulfate; 3,4-dihydroxy-1-tert-butylbenzene / 180 °C / 45 Torr 3.1: 3-chloro-benzenecarboperoxoic acid / tetrachloromethane / 4 h / 20 °C / |Cooling with ice 4.1: iodosylbenzene; tetrafluoroboric acid diethyl ether complex / dichloromethane; diethyl ether / |Inert atmosphere; |Molecular sieve View Scheme

copper(l) iodide; oxygen in dimethyl sulfoxide T=120°C; 54 h; Kinetics; chemoselective reaction;

lithium aluminium tetrahydride in diethyl ether Ambient temperature;

in tetrahydrofuran 1 h; Ambient temperature; Yield given. Title compound not separated from byproducts;

lithium aluminium tetrahydride; aluminium trichloride in diethyl ether; chloroform Reduction; 18 h; Heating;

1: pyridine; hydroxylamine hydrochloride / ethanol / 12 h / |Reflux 2: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 12.25 h / -10 - 20 °C / |Microwave irradiation 3: silver tetrafluoroborate; PPh3 gold(I) chloro complex / toluene / 18 h / 100 °C / |Microwave irradiation View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere; |Cooling with ice 1.2: |Inert atmosphere; |Cooling with ice 2.1: potassium hydrogensulfate; 3,4-dihydroxy-1-tert-butylbenzene / 180 °C / 45 Torr View Scheme

deuterium; palladium on activated charcoal in tetrahydrofuran P=2585.7 Torr; 18 h; Ambient temperature;