445-30-7Relevant articles and documents
Reactions of Monomethylthallium Diacetate and Amines
Knips, Ulrich,Huber, Friedo
, p. 434 - 436 (2007/10/02)
Decomposition of MeTl(OAc)2 (Me = CH3, HOAc = CH3COOH) in methanol in the presence of amines, like 2-, 3- and 4-picoline, benzylamines, dimethylaniline causes mainly N-methylation; the concurring O-methylation of acetate, giving MeOAc, is only a minor importance.The rate of N-methylation increases in the series 2-picoline /= pyridine 3-picoline 4-picoline /= dimethylaniline /= dimethylbenzylamine.Picolinic acid and MeTl(OAc)2 (molar ratio 1:1) react to give 25percent N-methylpicolinic acid and 75percent MeOAc; when the molar ratio was at least 2:1, a 1:1 mixture of N-methylpicolinic acid and the methylester of picolinic acid was produced.These results and rate changes in different solvents are explained by assuming MeTlOAc(+) being the active methylthallium electrophile. - Keywords: Monomethylthallium Diacetate, Amines, Methylation, Reaction Rate