1: 2-hydroxynonane With 1,10-phenanthroline; potassium tert-butylate; copper(l) chloride in o-di-fluorobenzene T=20°C; 0.166667 h; Inert atmosphere; 2: With 1-methyl-1H-imidazole; di-tert-butylazodicarboxylate; oxygen in o-di-fluorobenzene Reflux; 3: diazomethyl-trimethyl-silane With triphenylphosphine; isopropyl alcohol in o-di-fluorobenzene; diethyl ether T=60°C; Inert atmosphere;

copper acetylacetonate in tetrahydrofuran T=20°C; 20 h;

titanium tetrachloride; zinc in tetrahydrofuran; dichloromethane T=18 - 20°C; 12 h;

n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; methylene double anion donors, var. esters; Product distributionMechanism;

iodine T=150°C;

(trimethylstannyl)methyl-lithium T=-78°C;

phenyllithium in diethyl ether

diethyl ether; Petroleum ether

2: iodine / 150 °C View Scheme

1: (i) Et2O, (ii) aq. H2SO4, (iii) aq. KOH 2: iodine / 150 °C View Scheme