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Topic: Stability of tert-butyl tosylate  (Read 3996 times)

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Offline seahorse

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Stability of tert-butyl tosylate
« on: July 06, 2015, 05:44:20 AM »
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.

Offline discodermolide

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Re: Stability of tert-butyl tosylate
« Reply #1 on: July 06, 2015, 06:49:01 AM »
I think I might side with Hoffmann on this.
If you search Google for any particular compound, either via the CAS number or SMILES, especially if Aldrich don't sell it you always get hits. Companies offering to sell you it, ask for a quote, etc. They are just trying to get you to spend your money.
 
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