1601497-22-6Relevant articles and documents
Sodium iodide/tert-butyl(dimethyl)silyl chloride-induced isomerization of 2,3-allenols to 2(E)-enals
Zeng, Rong,Ma, Zhichao,Fu, Chunling,Ma, Shengming
, p. 1343 - 1358 (2014/05/06)
Through an unexpected C=C bond migration, 2(E)-enals were efficiently prepared highly stereoselectively in moderate to good yields via the sodium iodide/tert-butyl(dimethyl)silyl chloride (NaI/TBSCl)-mediated reaction of the easily available 2,3-allenols. Based on a careful mechanistic study, including control experiments and deuterium-labeling experiments, an electron-withdrawing substituent group in the 4 position has been proven to be crucial and a possible mechanism has been proposed.