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Rapid domino [3+2] cycloaddition, [4+2] cycloreversion, ring-opening and aromatisation of a fused oxanorbornane substrate

Johnstone, Mark D. and Pfeffer, Frederick M. 2015, Rapid domino [3+2] cycloaddition, [4+2] cycloreversion, ring-opening and aromatisation of a fused oxanorbornane substrate, Tetrahedron letters, vol. 56, no. 21, pp. 2754-2757, doi: 10.1016/j.tetlet.2015.04.025.

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Title Rapid domino [3+2] cycloaddition, [4+2] cycloreversion, ring-opening and aromatisation of a fused oxanorbornane substrate
Author(s) Johnstone, Mark D.
Pfeffer, Frederick M.ORCID iD for Pfeffer, Frederick M. orcid.org/0000-0002-5441-6437
Journal name Tetrahedron letters
Volume number 56
Issue number 21
Start page 2754
End page 2757
Total pages 4
Publisher Elsevier
Place of publication Amsterdam, The Netherlands
Publication date 2015-05-20
ISSN 0040-4039
1873-3581
Keyword(s) Aromatisation
Cycloaddition
Domino reaction
Fragmentation
One-pot
Retro-Diels-Alder
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
SHAPED CAVITY MOLECULES
ELECTRON-TRANSFER
ROUTE
ANHYDRIDES
LIGANDS
BRIDGES
SYSTEMS
SURFACE
FURAN
CAGES
Summary Heating a dioxa-bridged diene with a cyclobutane epoxide for 10 min under microwave conditions (150 °C) gave an unexpected aryloxanorbornane product (20%). This adduct is proposed to occur via a [3+2] dipolar cycloaddition, retro-Diels-Alder reaction, ring-opening and subsequent aromatisation.
Language eng
DOI 10.1016/j.tetlet.2015.04.025
Field of Research 030503 Organic Chemical Synthesis
0305 Organic Chemistry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2015, Elsevier
Persistent URL http://hdl.handle.net/10536/DRO/DU:30076863

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