ethanol; sodium ethanolate aufeinanderfolgendes Erhitzen mit wss. KOH und mitv wss. HCl;

CuF(PPh3)3*2MeOH; bis[2-(diphenylphosphino)phenyl] ether in toluene T=25°C; 15 h; Inert atmosphere; chemoselective reaction;

1: O2 2: Zn, aq. HCl View Scheme

1: phenyl-magnesium bromide With [3-[(1R,2R)-2-(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ylidene]copper(I) bromide in diethyl ether T=25°C; 0.25 h; Inert atmosphere; 2: non-3-en-2-one in diethyl ether T=25°C; 1.16667 h; Inert atmosphere; 3: With hydrogenchloride; water in diethyl ether

cyclooctadiene in water T=100°C; 4 h; Inert atmosphere;

1: diethylzinc With [3-[(1R,2R)-2-(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ylidene]copper(I) bromide in diethyl ether T=25°C; 0.25 h; Inert atmosphere; 2: non-3-en-2-one in diethyl ether T=25°C; 1.16667 h; Inert atmosphere; 3: With hydrogenchloride; water in diethyl ether

(i) NaOMe, MeOH, (ii) aq. KOH, (iii) aq. HCl; Multistep reaction;