Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 16, Pages 7098-7102Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301011e
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Funding
- National Science Foundation of China [21025207, 20975092]
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In collisional activation of protonated N-benzylaniline, the benzene loss from the benzyl moiety is actually not the result of dissociative proton transfer (PT). In fact, benzyl cation transfer (BCT) from the nitrogen to the anilinic ring (ortho or para position) is the key step for benzene loss. Such dissociation occurs only after the benzyl group migrating from the site with the highest benzylation nucleophilicity (nitrogen) to a different one (aromatic ring carbon), which is described as dissociative benzyl cation transfer.
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