Dissertation
Exploring the unique reactivity of unsaturated isocyanides
Doctor of Philosophy (Ph.D.), Drexel University
Jun 2024
DOI:
https://doi.org/10.17918/00010554
Abstract
A array of isocyanoalkenes, including aromatic, aliphatic, α,β-unsaturated, heterocyclic isocyanoalkenes, can be selectively synthesized via a copper catalyzed cross coupling - dehydration strategy. Utilizing this method, two natural products were prepared. The vinyl formamide as intermediate could be brominated, and then dehydrated to prepare a series of bromoisocyanoalkenes. The bromoisocyanoalkenes can undergo a [4+1] addition with NaSH to prepare thiazoles. This reaction was proceeded through a rare SNVπ displacement-cyclization pathway, producing an array of 4- or 5-substituted, or 4,5- disubstituted thiazoles. Additionally, an array of virtually unexplored isocyanoalkynes were prepared from bromoisocyanoalkenes. The chameleon-like isocyanoalkyne reacts with both nucleophiles and electrophiles and exhibits different reactivity under acidic or basic conditions.
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Details
- Title
- Exploring the unique reactivity of unsaturated isocyanides
- Creators
- Huan Tian
- Contributors
- Haifeng Ji (Advisor)
- Awarding Institution
- Drexel University
- Degree Awarded
- Doctor of Philosophy (Ph.D.)
- Publisher
- Drexel University; Philadelphia, Pennsylvania
- Number of pages
- ix, 218 pages
- Resource Type
- Dissertation
- Language
- English
- Academic Unit
- College of Arts and Sciences; Chemistry; Drexel University
- Other Identifier
- 991021890312904721