1: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 2: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 3: 74 percent / 1M-barium hydroxide / H2O / 1 h / Heating View Scheme

1: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 2: 100 percent / hydrogen / platinum oxide / acetic acid / 24 h 3: 76 percent / liquid ammonia, sodium / methanol View Scheme

1: 89 percent / thionyl chloride / diethyl ether / 16 h / Ambient temperature 2: pyridine / diethyl ether / 10 h / Ambient temperature View Scheme

pyridine in diethyl ether 10 h; Ambient temperature; Yield given;

1: 2.) triphenylphosphine, 2,2'-dithiodipyridine / 1.) chloroform, RT, 12 h, 2.) chloroform, 8 h, reflux, 12 h 2: 57 percent / triethylamine, (4-dimethylamino)pyridine / CH2Cl2 / 96 h / Ambient temperature 3: hydrogen / platinum oxide / acetic acid 4: 1.) 1M-diborane, 2.) barium hydroxide / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 1 h, 3.) water, RT, 12 h View Scheme