A Theoretical Investigation on the Model Wittig Reaction PH3CH2 + CH2O → PH3O + C2H4

R. Holler, H. Lischka

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Abstract

Ab initio SCF calculations have been performed for the model Wittig reaction given in the title. The basis sets used range from STO-3G to double-f plus polarization quality. Full geometry optimization has been performed with the STO-3G and double-f basis sets. The reaction takes place in an essentially concerted way. Starting from PH3CH2 + CH20 an oxaphosphetane ring is formed via a very small energy barrier. This ring system corresponds to a local minimum on the energy hypersurface. An energy barrier of ~25 kcal/mol is found for the dissociation of the oxaphosphetane ring into PH30 and C2H4. The total reaction energy is calculated to be about -45 to -50 kcal/mol.

Original languageEnglish
Pages (from-to)4632-4635
Number of pages4
JournalJournal of the American Chemical Society
Volume102
Issue number14
DOIs
StatePublished - Jul 1980

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