132606-80-5Relevant articles and documents
Preparation of β-Hydroxysulfides from 1,2,3-Thiadiazoles. Comparison of the Effect of Phenylmagnesium Bromide on α-Thio- and α-Selenoketones
Ganjian, Iraj
, p. 2037 - 2039 (2007/10/02)
Base decomposition of 4-substituted-phenyl-1,2,3-thiadiazoles at 78 deg C resulted in 2-(4-substituted-phenyl)-ethynylthiolate anions which were immediately reacted with α-bromoketones to give a series of α-(2-ethynyl) thioketones.Unlike the selenophilic reaction of the Grignard reagents with α-selenoketones, the carbonyl group was the site of nucleophilic attack and the reaction of the α-thioketones with phenylmagnesium bromide gave the corresponding β-hydroxysulfides.The difference in mode of action toward the Grignard reagents was attributed to the difference in the bond strengths between carbon and the hetero-atoms.
