Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols

Aliphatic thiols are in high demand materials chemistry. Herein, a synthesis of thio-derivatives 1-hexene vinylidene dimer is described. The approach, based on hydroalumination reaction with further replacement the organoaluminum function sulfur using thiourea or dimethyl disulfide, provides anti-Markovnikov products, 2-butyloctane-1-thiol 5-(methylsulfanylmethyl)undecane, moderate yields. phosphorus pentasulfide presence catalytic amounts (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) selectively gives Markovnikov product, 5-methylundecane-5-thiol, yield up to 77%.