1427778-16-2Relevant articles and documents
Subtle electronic effects in metal-free rearrangement of allenic alcohols
Sabbasani, Venkata R.,Mamidipalli, Phani,Lu, Huijie,Xia, Yuanzhi,Lee, Daesung
, p. 1552 - 1555 (2013/06/26)
A general and stereoselective rearrangement of allenic alcohols to (E,E)-1,3-dien-2-yl triflates and chlorides was developed under metal-free conditions. Subtle electronic effects of the alkyl and aryl substituents on the carbon bearing the hydroxyl group has a profound impact on the reaction rate and efficiency such that vinyl triflates were obtained from electron-deficient substrates and trimethylsilyl triflate whereas vinyl chlorides were generated with an electron-rich substrate and trimethylsilyl chloride.