1: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 10 min. 2: 89 percent / DMAP, Py / 16 h / Ambient temperature 3: 78 percent / NaH, DBU / tetrahydrofuran / 3.5 h / Ambient temperature View Scheme

1: TolS(O)CH2Cl With isopropylmagnesium chloride in tetrahydrofuran T=-78°C; 2: N-methylaniline With n-butyllithium in tetrahydrofuran T=-78 - -40°C; 3: chloroformic acid ethyl ester in tetrahydrofuran T=-40°C;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene Heating;

3-chloro-benzenecarboperoxoic acid

1: TolS(O)CH2Cl With isopropylmagnesium chloride in tetrahydrofuran T=-78°C; 2: N-Benzylbenzylamine With n-butyllithium in tetrahydrofuran T=-78 - -40°C; 3: chloroformic acid ethyl ester in tetrahydrofuran T=-40°C;

1: TolS(O)CH2Cl With isopropylmagnesium chloride in tetrahydrofuran T=-78°C; 2: N-Benzylbenzylamine With n-butyllithium in tetrahydrofuran T=-78 - -40°C; 1 h;

View Scheme

n-butyllithium; tert.-butyl lithium; diisopropylamine; lithium diisopropyl amide multistep reaction, 1.) THF, -65 deg C; 2.) 3.) THF, -70 deg C; in step 2.) reagent also KH; in 2.) 3.) temperature also -80 - -90 deg C; substrate effect; one-carbon homologation of ketones and aldehydes to ketones; Product distribution;

1.1: LDA / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 °C 2.1: pyridine; 4-(dimethylamino)pyridine / 15 h / 20 °C 3.1: Ph2NLi / tetrahydrofuran View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 10 min. 2: 89 percent / DMAP, Py / 16 h / Ambient temperature 3: 78 percent / NaH, DBU / tetrahydrofuran / 3.5 h / Ambient temperature 4: 2.) H2O / 1.) THF, 0 deg C, 30 min. View Scheme