97552-15-3Relevant academic research and scientific papers
On the Origin of E/Z Selectivity in the Modified Julia Olefination - Importance of the Elimination Step
Robiette, Raphael,Pospisil, Jiri
, p. 836 - 840 (2013)
The mechanism and origin of high E selectivity in the modified Julia olefination of aromatic aldehydes have been explored by computational and experimental means. Reversibility of addition and hence selectivity of the formation of sulfinate 5 is very variable and depends on the nature of the sulfone substrate. However, in all cases, elimination occurs through a concerted antiperiplanar and synperiplanar mechanism for sulfinates anti-5 and syn-5, respectively. Both syn and anti diastereomeric pathways thus lead preferentially to the (E)-alkene. Copyright
