Investigation of Reactions Involving Pentacoordinate Intermediates [electronic resource] : The Mechanism of the Wittig Reaction / by Peter A. Byrne.
By: Byrne, Peter A [author.].
Contributor(s): SpringerLink (Online service).
Material type:
BookSeries: Springer Theses, Recognizing Outstanding Ph.D. Research: Publisher: Berlin, Heidelberg : Springer Berlin Heidelberg : Imprint: Springer, 2012Description: XVI, 231 p. 208 illus., 30 illus. in color. online resource.Content type: text Media type: computer Carrier type: online resourceISBN: 9783642320453.Subject(s): Chemistry | Analytical biochemistry | Chemistry, Organic | Chemistry | Organic Chemistry | Theoretical and Computational Chemistry | Analytical ChemistryDDC classification: 547 Online resources: Click here to access online Introduction to the Wittig reaction & discussion of the mechanism -- Wittig reactions of aldehydes bearing a β-heteroatom substituent -- A convenient chromatography-free method for the purification of alkenes produced in the Wittig reaction -- Experimental.
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.
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