Intramolecular Diels–Alder Reaction of a Biphenyl Group in a Strained meta-Quaterphenylene Acetylene

At elevated temperatures, a strained, cyclic meta-quaterphenylene acetylene undergoes an intramolecular cyclization reaction to form benz­[e]­indeno­[1,2,3-hi]­acephenanthrylene. This reaction represents an example of a Diels–Alder reaction at the 2-, 1-, 1′-, and 2′-positions of a biphenyl derivati...

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Published in:Journal of organic chemistry 2024-07, Vol.89 (13), p.9620-9626
Main Authors: Mittal, Komal, Pham, Ashley V., Davis, Amanda G., Richardson, Abigail D., De Hoe, Clement, Dean, Ryan T., Baird, Vi, McDonald, Ashley Ringer, Frantz, Derik K.
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cited_by cdi_FETCH-LOGICAL-a430t-b52f327800fd533e3098713dd26d9b3b67ea320dd3a00441a99cf1563249ae1f3
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container_end_page 9626
container_issue 13
container_start_page 9620
container_title Journal of organic chemistry
container_volume 89
creator Mittal, Komal
Pham, Ashley V.
Davis, Amanda G.
Richardson, Abigail D.
De Hoe, Clement
Dean, Ryan T.
Baird, Vi
McDonald, Ashley Ringer
Frantz, Derik K.
description At elevated temperatures, a strained, cyclic meta-quaterphenylene acetylene undergoes an intramolecular cyclization reaction to form benz­[e]­indeno­[1,2,3-hi]­acephenanthrylene. This reaction represents an example of a Diels–Alder reaction at the 2-, 1-, 1′-, and 2′-positions of a biphenyl derivative, a region analogous to the bay regions of perylene and other periacenes. The reaction proceeds cleanly with high conversion. Kinetics studies of a methylated derivative reveal that the ΔG ‡ for the reaction is ∼40–41 kcal/mol, and computational models predict a similar value of G rel for the transition state of a concerted [4 + 2]-cycloaddition.
doi_str_mv 10.1021/acs.joc.2c02280
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title Intramolecular Diels–Alder Reaction of a Biphenyl Group in a Strained meta-Quaterphenylene Acetylene
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