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Dynamic intermediates in the radical cation diels–alder cycloaddition: lifetime and suprafacial stereoselectivity

Abstract:

Cation radical Diels–Alder cycloadditions proceed via an acyclic intermediate that exists on a flat region of the potential energy surface. Competition between cyclization and C–C bond rotation results in varying levels of suprafacial stereoselectivity. Quasi-classical trajectories were used to explore reaction dynamics on this surface. Even though there is no discernible energy barrier toward cyclization, a dynamically stepwise process is found, for which the acyclic intermediate is found to...

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Publication status:
Published
Peer review status:
Peer reviewed

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Files:
  • (Accepted manuscript, pdf, 273.6KB)
Publisher copy:
10.1021/acs.orglett.8b00737

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
ORCID:
0000-0001-9091-0443
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Hilda's College
Role:
Author
ORCID:
0000-0002-0104-4166
More from this funder
Funding agency for:
Tan, J
Grant:
National Science Scholarship
More from this funder
Grant:
ModellinginChemical Sciences(EP/L015722/1
EPSRCCentrefor DoctoralTraininginTheory
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
20
Issue:
10
Pages:
2821-2825
Publication date:
2018-05-09
Acceptance date:
2018-05-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pmid:
29741386
Source identifiers:
853066
Language:
English
Pubs id:
pubs:853066
UUID:
uuid:379c8c6e-e25b-4e80-a39d-04c3a43f8349
Local pid:
pubs:853066
Deposit date:
2018-05-22

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