Thesis
The synthesis of diethyl isocyanomethylphosphonate as a precursor to isocyanoalkynes
Master of Science (M.S.), Drexel University
Jun 2026
DOI:
https://doi.org/10.17918/00011457
Abstract
Nature was the first to combine the functionality of isocyanides and alkynes, not on Earth, but in interstellar gas clouds. The products of this celestial pairing, isocyanoalkynes, are a rare family of compounds that unite the versatility of the isocyanide with that of the alkyne yet remain largely unexplored despite the synthetic potential their unique structure offers. This thesis describes research to address that gap by developing a more efficient synthetic route to isocyanoalkynes. The proposed synthesis targeted bromoisocyanomethylphosphonate as a key reagent to convert a simple aldehyde to an [alpha]-bromoisocyanoalkene intermediate that, upon elimination, would deliver an isocyanoalkyne. Central to this approach is the construction of the reagent itself. The route described starts with the conversion of aminomethylphosphonic acid to the corresponding formamide, followed by dehydration. Successfully developing this route reduces what was previously a five-step synthesis of isocyanomethylphosphonate to just two, with a dramatic improvement in overall yield. These advances lay the groundwork for a more accessible route to isocyanoalkynes, potentially making them a more viable addition to researchers' synthetic toolkit and enabling a fuller exploration of their reactivity.
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Details
- Title
- The synthesis of diethyl isocyanomethylphosphonate as a precursor to isocyanoalkynes
- Creators
- Vanessa Penelope Lambrou
- Contributors
- Fraser F. Fleming (Advisor)
- Awarding Institution
- Drexel University
- Degree Awarded
- Master of Science (M.S.)
- Publisher
- Drexel University
- Number of pages
- vi, 32 pages
- Resource Type
- Thesis
- Language
- English
- Academic Unit
- College of Arts and Sciences; Chemistry; Drexel University
- Other Identifier
- 991022193197604721