The action of sodium hydrogen telluride on olefins

Article abstract of DOI:10.1016/S0040-4020(01)87834-0

The action of sodium hydrogen telluride, NaTeH, on non electrophilic carbon-arbon double bonds has been investigated.The reaction is found to be very sensitive to the substituents on the ethylenic linkage. Whereas phenyl conjugated olefins are reduced to alkylbenzenes,the reagent adds to isolated mono and disubstituted double bonds leading to organotellurium derivatives and with gem-disubstituted ones it leads to a mixture of reduction and addition products. These results are interpreted in terms of a radical pair mechanism involving hydrogen atom transfer from hydrogen telluride,HTe^- to the double bond.