1: 91 percent / Bu3SnH, AIBN / benzene / 2 h / Heating 2: ethyl acetate / 18 h / Ambient temperature 3: dimethyldioxirane / CH2Cl2 / -78 °C 4: Et3N / CH2Cl2 / 18 h / Ambient temperature 5: 1.) Zn, TiCl4 / 1.) THF, r.t., 30 min; CH2Cl2, r.t., 30 min, 2.) 15 min 6: 88 percent / aq. K2CO3 / methanol / 18 h / Heating 7: (COCl)2, DMF / CH2Cl2 / 2 h 8: DMAP / benzene / 0.5 h / Heating 9: benzene / 1 h / Heating; Irradiation View Scheme

1: 85 percent / t-BuOK / 2-methyl-propan-2-ol / 1.) reflux, 30 min, 2.) reflux, 2 h 2: aq. HCl / 48 h / Heating 3: Heating 4: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min, 2.) -78 deg C, 1 h; -78 deg C to r.t. 5: (COCl)2, DMF / benzene / 3 h / Ambient temperature 6: 1.) Na / 1.) THF, 2.) 10 min 7: 91 percent / Bu3SnH, AIBN / benzene / 2 h / Heating 8: ethyl acetate / 18 h / Ambient temperature 9: dimethyldioxirane / CH2Cl2 / -78 °C 10: Et3N / CH2Cl2 / 18 h / Ambient temperature 11: 1.) Zn, TiCl4 / 1.) THF, r.t., 30 min; CH2Cl2, r.t., 30 min, 2.) 15 min 12: 88 percent / aq. K2CO3 / methanol / 18 h / Heating 13: (COCl)2, DMF / CH2Cl2 / 2 h 14: DMAP / benzene / 0.5 h / Heating 15: benzene / 1 h / Heating; Irradiation View Scheme

1: 1.) MeLi / 1.) Et2O, DME, 0 deg C, 5 min, 2.) 30 s 2: ethyl acetate / 18 h / Ambient temperature 3: dimethyldioxirane / CH2Cl2 / -78 °C 4: Et3N / CH2Cl2 / 18 h / Ambient temperature 5: 1.) Zn, TiCl4 / 1.) THF, r.t., 30 min; CH2Cl2, r.t., 30 min, 2.) 15 min 6: 88 percent / aq. K2CO3 / methanol / 18 h / Heating 7: (COCl)2, DMF / CH2Cl2 / 2 h 8: DMAP / benzene / 0.5 h / Heating 9: benzene / 1 h / Heating; Irradiation View Scheme

1: Heating 2: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 10 min, 2.) -78 deg C, 1 h; -78 deg C to r.t. 3: (COCl)2, DMF / benzene / 3 h / Ambient temperature 4: 1.) Na / 1.) THF, 2.) 10 min 5: 91 percent / Bu3SnH, AIBN / benzene / 2 h / Heating 6: ethyl acetate / 18 h / Ambient temperature 7: dimethyldioxirane / CH2Cl2 / -78 °C 8: Et3N / CH2Cl2 / 18 h / Ambient temperature 9: 1.) Zn, TiCl4 / 1.) THF, r.t., 30 min; CH2Cl2, r.t., 30 min, 2.) 15 min 10: 88 percent / aq. K2CO3 / methanol / 18 h / Heating 11: (COCl)2, DMF / CH2Cl2 / 2 h 12: DMAP / benzene / 0.5 h / Heating 13: benzene / 1 h / Heating; Irradiation View Scheme

tetra-n-propyl-diborane; hydrogen in n-heptane T=200°C; P=75006 Torr; 4 h; various concentrations; further substituted naphthalenes; Product distributionKinetics;

tetra-n-propyl-diborane; hydrogen in n-heptane T=200°C; P=75006 Torr; 0.5 h; Product distribution;

tetra-n-propyl-diborane; hydrogen in toluene T=200°C; P=75006 Torr; 4 h; Product distribution;

diethyl ether; magnesium

aluminium trichloride

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