Sigmatropic rearrangements via the use of heteroallenes (ketenimine & keteniminium salts)
LE3 .A278 2020
Master of Science
This thesisis split into two distinct sections each section corresponding to different heteroallenes (ketenimines and keteniminium salts). In the first section, diverse strategies were used to synthesize ketenimines. Although they are difficult to isolate because of their reactivity; their synthesis was successfully achieved. The idea was to use these highly reactive ketenimines to facilitate Claisen rearrangements, and expand a rearrangement that normally involves ketenes. This route eventually brought us to another heteroallene source: keteniminium salts. The second section deals with the chemistry of the activation of amides. This chemistry is applied to the generation of a keteniminium salt. Recent works have shown their potential in sigmatropic rearrangements. These works have shown that keteniminium salts could undergo sigmatropic rearrangements with allylic ethers. The idea was to build on this body of work and to further develop the versatility of the method.
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