![Investigation of the Cycloaddition Reactions of Some New Azophosphonates and Azobis(phosphonates): A New Manifestation of the Staudinger Synthesis](https://ecommons.udayton.edu/assets/images/placeholder-thumbnail.jpg)
Investigation of the Cycloaddition Reactions of Some New Azophosphonates and Azobis(phosphonates): A New Manifestation of the Staudinger Synthesis
Presenter(s)
Joshua Killian
Files
Description
Newly synthesized azo-compounds, with one or two pendant phosphonate groups, have recently been shown to react easily with conjugated dienes, such as 2,3-dimethylbutadiene or cyclopentadiene. In both cases, the ensuing [4+2] cycloaddition reactions have led to the preparation, isolation, and full characterization of a series of products. However, there is no clear evidence in chemical literature on [2+2] cycloaddition reactions with an azo-component. These [2+2] reactions are rare in principle, and have been typically conducted with an alkene and a ketene component. This study investigated the question as to whether azo-compounds can participate in such reactions, in place of the alkene component. Investigation focused on diphenylketene, which was reacted with several azobis(phosphonates) or azophosphonates, at ambient temperature. The 1H-, 13C- and 31P-NMR spectroscopic results confirmed that a ring structure was formed, but the data suggested that instead of a [2+2] cycloaddition, resulting in a four-membered ring, a six-membered ring formed, the product of a formal [2+2+2] cycloaddition. The Staudinger synthesis, used for the preparation of β-lactam rings, provides a possible explanation for the mechanism of formation of the six-membered ring.
Publication Date
4-24-2019
Project Designation
Independent Research
Primary Advisor
Vladimir A. Benin
Primary Advisor's Department
Chemistry
Keywords
Stander Symposium project
Recommended Citation
"Investigation of the Cycloaddition Reactions of Some New Azophosphonates and Azobis(phosphonates): A New Manifestation of the Staudinger Synthesis" (2019). Stander Symposium Projects. 1541.
https://ecommons.udayton.edu/stander_posters/1541
![Investigation of the Cycloaddition Reactions of Some New Azophosphonates and Azobis(phosphonates): A New Manifestation of the Staudinger Synthesis](https://ecommons.udayton.edu/assets/images/placeholder-thumbnail.jpg)