The Reaction of 2,3,4-Trichlorothiophene with Alkyllithium Reagents

Article abstract of DOI:10.1007/BF00798328

2,3,4-Trichlorothiophene undergoes metal-hydrogen exchange with one equivalent of butyllithium in THF at -78 deg C to give trichloro-2-thienyllithium in 91percent yield.No metal-halogen exchange is observed to have taken place.With t-butyllithium under similar conditions, however, the metal-halogen exchange reaction occurs but only to the extent of 8percent; the main reaction remains to be the metal-hydrogen exchange. 2,3,4-Trichlorothiophene reacts with two equivalents of butyllithium in ether at -5 deg C to give 3,4-dichloro-2,5-dilithiothiophene in 96percent yield. - Keywords: 3,4-Dichloro-2,5-dilithiothiophene; Lithium-chlorine exchange; Trichloro-2-thienyllithium; 2,3,4-Trichlorothiophene