A General Hypothesis for the Mechanism of the Wittig Reaction

References

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• Eight stereoisomeric oxaphosphetanes can be formed in the initial stage of the reactions under discussion here. Two of them (enantiomers), which would lead to cis-alkene, arise via less sterically hindered transition states than the others
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• Theoretical chemists7 believe that, in the Wittig reaction under salt-free conditions, C-C bond formation runs slightly ahead of P-O bond formation. However, their model bears little relationship to real Wittig reactions
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• Firestone , R. A. (Private Communication, Dec. 9, 1986) has suggested an intriguing extension of the Born-Oppenheimer Principle to account for the preferred formation of Cis-alkenes by the reaction of unstable ylides with aldehydes via a spin paired diradical intermediate. This will be discussed in a subsequent paper
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