1,5-diazabicyclo[5.4.0]undeca-5-ene in tetrahydrofuran 2.5 h; Ambient temperature;

1: 35.8 percent / pyridine / Ambient temperature 2: 100 percent / NaOCH3 / methanol; tetrahydrofuran / 1 h / Ambient temperature 3: 95 percent / pyridine / Ambient temperature 4: 94 percent / N-bromosuccinimide (NBS), α,α'-azobis(isobutyronitrile) (AIBN) / CCl4 / 0.5 h / 65 °C 5: 40 mg / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

1: 95 percent / pyridine / Ambient temperature 2: 94 percent / N-bromosuccinimide (NBS), α,α'-azobis(isobutyronitrile) (AIBN) / CCl4 / 0.5 h / 65 °C 3: 40 mg / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

1: 94 percent / N-bromosuccinimide (NBS), α,α'-azobis(isobutyronitrile) (AIBN) / CCl4 / 0.5 h / 65 °C 2: 40 mg / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

1: 100 percent / NaOCH3 / methanol; tetrahydrofuran / 1 h / Ambient temperature 2: 95 percent / pyridine / Ambient temperature 3: 94 percent / N-bromosuccinimide (NBS), α,α'-azobis(isobutyronitrile) (AIBN) / CCl4 / 0.5 h / 65 °C 4: 40 mg / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

phosphoric acid in methanol T=60°C; 5 h; Yield given. Yields of byproduct given;

palladium; 1-methyl-naphthalene

1: aluminium chloride; dichloromethane 2: amalgamated zinc; aqueous HCl 3: PCl5; benzene / anschliessendes Behandeln mit SnCl4 4: palladium; 1-methyl-naphthalene View Scheme

1: PCl5; benzene / anschliessendes Behandeln mit SnCl4 2: palladium; 1-methyl-naphthalene View Scheme

1: amalgamated zinc; aqueous HCl 2: PCl5; benzene / anschliessendes Behandeln mit SnCl4 3: palladium; 1-methyl-naphthalene View Scheme