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Chemistry - Organic Chemistry | Investigation of Reactions Involving Pentacoordinate Intermediates - The Mechanism of the Wittig

Investigation of Reactions Involving Pentacoordinate Intermediates

The Mechanism of the Wittig Reaction

Series: Springer Theses

Byrne, Peter A

2012, XVI, 231 p. 208 illus., 30 illus. in color.

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  • Nominated by University College Dublin as an outstanding PhD thesis
  • Describes the first example of an effect common to examples of all Li salt-free Wittig reactions
  • Outlines the development of a new chromatography-free method for the removal of phosphine oxide from the alkene crude product of the Wittig reaction
In this thesis, the author outlines the discovery of an effect common to representative examples of all Li salt-free Wittig Reactions. The implications of such a universally applicable effect are that all such Wittig reactions occur through the same mechanism. Although the Wittig reaction was first discovered in 1953, its reaction mechanism has never been definitively settled with many different variants proposed and disproved. The work in this thesis shows conclusively that for [2+2] cycloadditions all Wittig reactions occur by the same irreversible mechanism. In addition, the author also describes a new chromatography-free method for the removal of phosphine oxide from the alkene crude product of the Wittig reaction. The work in this thesis has led to several publications in high-profile journals.

Content Level » Research

Keywords » Alkene Z/E Ratio - Kinetic Control in the Wittig Reaction - Oxalyl Chloride - Oxaphosphetane cis/trans Ration - Phosphine Oxide Removal - Wittig Reaction Mechanism - Ylide Carbonyl [2+2] Cycloaddition

Related subjects » Analytical Chemistry - Organic Chemistry - Theoretical and Computational Chemistry

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