73568-80-6Relevant academic research and scientific papers
Wittig reaction: Role of steric effects in explaining the prevalent formation of Z olefin from nonstabilized ylides
Baccolini, Graziano,Delpivo, Camilla,Micheletti, Gabriele
, p. 1291 - 1302 (2012/11/13)
For understanding the mechanism involved in the Wittig reaction, it is important to know the factors which influence the stability of 1,2-oxaphosphetane intermediates with pentacoordinate phosphorus; in these intermediates, the steric factor plays a predominant role. Studying the Wittig reaction between nonstabilized ylides and different aldehydes, we noted that the stereochemical outcome driving toward Z-olefin formation was influenced only by different steric factors. The proposed mechanism differs from those previously reported because it underlines the fundamental role of the two cis/trans oxaphosphetane intermediates with the oxygen atom in equatorial position.
