rings. Tosyl groups can be removed from N-tosylamides almost instantaneously, using SmI2 in conjunction with distilled water and an amine base. The reaction is even effective for deprotection of sensitive substrates such as aziridines: In the Markó-Lam deoxygenation, an alcohol could be almost instantaneously deoxygenated by reducing their toluate ester in presence of SmI2. The applications of SmI2 have been reviewed. The book Organic Synthesis Using Samarium Diiodide, published in 2009, gives a detailed overview of reactions mediated by SmI2. References Iodides Samarium compounds Lanthanide halides One-electron reducing agents Reagents for organic chemistry