ammonia; lithium in diethyl ether

ammonia

in tetrahydrofuran

in tetrahydrofuran Heating;

ammonia

diethyl ether; copper(l) chloride

1: CaCl2, aq. HCl 2: tBuOH, Li / tetrahydrofuran / 4 h / Heating View Scheme

ON(CH3)3; n-BuLi; COCl2 in tetrahydrofuran; diethyl ether; dichloromethane cooling suspn. of ONMe3 to -78°C, addn. of Fe(CO)5; deprotonation of HCCC(t-Bu)2OH with n-BuLi in ether at room temp.; reacting solns. by stirring at room temp. for 1 h; evapn., dissolving in CH2Cl2, addn. of COCl2 in ether; changing solvents to petroleum ether, filtering, concd. of soln., chromy.; evapn., sublimation at room temp.; elem. anal.;

1: CaCl2, aq. HCl 2: tBuOH, Li / tetrahydrofuran / 4 h / Heating 3: AcOOH, Na2CO3 / CH2Cl2 / 26 h / 25 °C 4: pentane / 19 h / Irradiation View Scheme