928056-49-9Relevant academic research and scientific papers
Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of β-chloro-α-iodo- α,β-unsaturated esters
Lemay, Alison B.,Vulic, Katarina S.,Ogilvie, William W.
, p. 3615 - 3618 (2006)
The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-β-chloro-α-iodo- α,β-unsaturated esters by exposure to Bu4-NI
Single-isomer iodochlorination of alkynes and chlorination of alkenes using tetrabutylammonium iodide and dichloroethane
Ho, Michael L.,Flynn, Alison B.,Ogilvie, William W.
, p. 977 - 983 (2007/10/03)
(Chemical Equation Presented) The efficient formation of single-isomer, differentially halogenated alkenes and alkanes is described. These structures were generated by treatment of the appropriate alkyne or alkene with tetrabutylammonium iodide in refluxing dichloroethane. This process is highly selective as evidenced by control experiments using ICl. Treatment of the same alkenes and alkynes directly with iodine monochloride resulted in complex, inseparable mixtures of regio- and stereoisomers. Mechanistic studies indicated that the Bu4NI reaction most likely proceeded through the slow generation of ICl. Complexation of ICl with Bu4NI is also a key controlling element that leads to perfect regio-, chemo-, and stereoselectivity in these processes.
