Wittig Reaction: Role of Steric Effects in Explaining the Prevalent Formation of Z Olefin from Nonstabilized Ylides

G Baccolini, C Delpivo, G Micheletti

Index: Baccolini, Graziano; Delpivo, Camilla; Micheletti, Gabriele Phosphorus, Sulfur and Silicon and the Related Elements, 2012 , vol. 187, # 11 p. 1291 - 1302

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Abstract

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. ...