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Studies of 2,1-benzothiazine, silver-catalyzed rearrangement and 1,5-hydride shift

Authors: Huang, Chaofeng, 1978-;

Studies of 2,1-benzothiazine, silver-catalyzed rearrangement and 1,5-hydride shift

Abstract

Title from PDF of title page (University of Missouri--Columbia, viewed on Feb 26, 2010). ; The entire thesis text is included in the research.pdf file; the official abstract appears in the short.pdf file; a non-technical public abstract appears in the public.pdf file. ; Thesis advisor: Dr. Michael Harmata. ; Vita. ; Ph.D. University of Missouri--Columbia 2009. ; [ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT REQUEST OF AUTHOR.] Dimethyl sulfoximine was used to synthesize benzothiazines by coupling reaction. When the substrate is dibromodibenzaldehyde, water was added to complete the reaction in meso product. Also some of the 2,1-benzothiazine's derivatives were synthesized. A novel method for the rearrangement from propargylic sulfinates to allenic sulfones by silver catalysis was discovered. This reaction works under very mild conditions with quantitative yield in fast mode. Also it's scalable. By silver catalysis, the synthesis oxazolines from Nproparglamides was also discovered. This reaction was very fast, robust and in high yield. Dichlorocyclopentanone derivative reacted with alkenes to obtain 1,5-hydride shift product. It shows oxyallylic cations and alkene can react with each other in the ene-like hydride shift reaction. This result was supported by computational analysis. ; Includes bibliographical references.

Country
United States
Related Organizations
Keywords

Chemical reactions, 500, 540, Organic compounds -- Synthesis, Silver catalysts

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
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