Hi all,
This old paper (H. M. R. Hoffmann, J. Chem. Soc., 1965, 6748-6753) describes that tert-butyl tosylate is very unstable (the half-life in acetonitrile at 0 °C is 63 min) due to spontaneous E1 reaction. I think it is likely, but I found one paper (J.G. Kim, Synlett 2007, 16, 2501-2504) in which the authors synthesized t-BuOTs in 79% yield at 120 °C by using Indium metal as a catalyst. t-BuOTs is also on catalogs of some reagent companies on the web (but I am not sure if it can be really purchased). So I am confused about the stability.
I actually traced the synthesis by Kim but failed (seems decomposed to TsOH). Has anyone synthesized tert-butyl tosylate or used it for any reactions? Or can anyone assert that the compound is unstable and the paper is a mistake or hoax. I would appreciate your help.