New Synthetic “tricks”. [Et3NH][Sn(SPh3)] and Bu2SnH2, two useful reagents for the reduction of azides to amines
✍ Scribed by Martí Bartra; Fèlix Urpí; Jaume Vilarrasa
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 326 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Treatment of Sn(SPh)z with PhSH and Et3N affords a tin(II) complex, soluble in organic solvents, which is the best reducing agent for azides reported so far. Bu2SnH2. although not so reactive, also shows several advantages with regard to the standard reducing agents for azides. such as its solubility in most solvents or its scarce reactivity with water. For a long time, the reducing agents SnC12 and Bu$nH and Lewis' acid SnClq were almost the only tin-based reagents utilised in organic synthesis. Nowadays, there is a boom in this connection, owing to the interesting synthetic applications of 0-stannyl enol ethers, stannoxanes, allylstannanes and vinylstannanes (among others), whose preparation requires other reagents such as R,$nX, Bu2Sn0, etc.' We describe here the properties of a new tin(Il) reagent, [Et3NH][Sn(SPh)d, arising from the known Sn(SPh)2,2 PhSH, and Et3N, as well as those of Bu2SnH2,3 with regard to the reduction of azides to amines.