Gas-Phase Intramolecular Cyclization of Argentinated N-Allylbenzamides View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2015-05

AUTHORS

Hezhi Sun, Yunfeng Chai, Zhe Jin, Cuirong Sun, Yuanjiang Pan

ABSTRACT

The fragmentations of argentinated N-allylbenzamides have been exhaustively studied through collision-induced dissociation and through deuterium labeling. The intriguing elimination of AgOH is certified as the consequence of intramolecular cyclization between terminal olefin and carbonyl carbon following proton transfer to carbonyl oxygen, rather than simple enolization of amide. Linear free energy correlations and density functional theory (DFT) calculations were performed to understand the competitive relationship between AgOH loss and AgH loss, which results from the 1,2-elimination of α-hydrogen (to the amido nitrogen) with the silver. More... »

PAGES

826-832

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s13361-015-1079-0

DOI

http://dx.doi.org/10.1007/s13361-015-1079-0

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1038255051

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/25707590


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