Theoretical study of the Wittig reaction of cyclic ketones with phosphorus ylide

Journal of Molecular Modeling
Nisha Jarwal, Pompozhi Protasis Thankachan

Abstract

The Wittig reaction of cyclopropanone, cyclobutanone and cyclopentanone with phosphorus ylide (Me3P = CH2) in gas phase was investigated computationally at B3LYP/6-31G** level of theory. In the Wittig reaction of cyclic ketones, two transition states (TS1 and TS2), corresponding to formation and decomposition of oxaphosphetane (OP) were located and investigated. Two loosely bound intermediates, a reactant complex (RC) and a product complex (PC) were also found. In the reaction of cyclopropanone, cyclobutanone and cyclopentanone, two oxaphosphetanes (OP1 and OP2) were predicted. OP1 initially formed was converted into OP2 by pseudorotation. In contrast to the reactions with cyclobutanone and cyclopentanone, an early TS1 was found in the reaction of cyclopropanone. The order of first activation energy barrier relative to reactant total energy was found to be cyclopropanone (-4.97 kcal mol(-1)) < cyclobutanone (0.30 kcal mol(-1)) < cyclopentanone (3.60 kcal mol(-1)).

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Feb 16, 2006·Journal of the American Chemical Society·Raphaël RobietteJeremy N Harvey
Apr 6, 2006·Journal of the American Chemical Society·Robert D Bach, Olga Dmitrenko

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Citations

Oct 11, 2019·European Journal of Organic Chemistry·Thomas A KingDavid R Spring
Mar 26, 2021·Advances in Pharmacological and Pharmaceutical Sciences·Zeleke DigafieRajalakshmanan Eswaramoorthy
Oct 19, 2019·The Journal of Organic Chemistry·Paola FarfánAlbeiro Restrepo
Apr 16, 2020·The Journal of Organic Chemistry·Eduardo ChamorroLuis R Domingo

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