thionyl chloride T=20°C; 1 h;

Lawesson's reagent in benzene 1 h; Ambient temperature;

tert-butylhypochlorite in chloroform; N,N-dimethyl-formamide

1: benzene / Heating 2: tBuOCl / CHCl3; dimethylformamide View Scheme

1: 47 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 24 h / Heating 2: 68 percent / NaN3, tetrabutylammonium bromide, NaI / CH2Cl2; H2O / 12 h / Ambient temperature 3: 59 percent / conc. H2SO4 / 120 h / Ambient temperature 4: 51 percent / 1 N NaOH / 0.25 h / Ambient temperature View Scheme