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Successive rotonation of an N‐heterocyclic imine derived carbonyl: Superelectrophilic dication versus masked acylium ion

Abstract:

Carbonyl cations are among the most commonly invoked reactive intermediates in organic synthesis. While Olah pioneered superacids to provide a “stable ion” environment for their study in situ, isolated examples are rare. Here, we disclose successive protonation of an N‐heterocyclic imine (NHI) derived carbonyl compound (IDippN)2CO, 2, to the monocation [(IDippN)(IDippNH) CO]+, [3]+, and the doubly protonated dication [(IDippNH)2CO]2+, [4]2+. [3]+ represents a rare example of an N‐protonated c...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/anie.201810709

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Inorganic Chemistry
Oxford college:
Queens College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Inorganic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Inorganic Chemistry
Role:
Author
ORCID:
0000-0003-4546-3984
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Inorganic Chemistry
Oxford college:
Queens College
Role:
Author
ORCID:
0000-0001-9998-9434
Magnus Ehrnroothin Säätiö More from this funder
Emil Aaltosen Säätiö More from this funder
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
57
Issue:
50
Pages:
16559-16563
Publication date:
2018-11-15
Acceptance date:
2018-10-24
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pmid:
30354008
Source identifiers:
936551
Language:
English
Keywords:
Pubs id:
pubs:936551
UUID:
uuid:370fa2f1-64e8-43dd-bea2-30a6da005b49
Local pid:
pubs:936551
Deposit date:
2019-02-21

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