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

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

Journal of organic chemistry, 2023-01 [Periódico revisado por pares]

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Título:
Intramolecular Diels-Alder Reaction of a Biphenyl Group in a Strained meta -Quaterphenylene Acetylene
Autor: 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
É parte de: Journal of organic chemistry, 2023-01
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: At elevated temperatures, a strained, cyclic -quaterphenylene acetylene undergoes an intramolecular cyclization reaction to form benz[ ]indeno[1,2,3- ]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 Δ for the reaction is ∼40-41 kcal/mol, and computational models predict a similar value of for the transition state of a concerted [4 + 2]-cycloaddition.
Editor: United States
Idioma: Inglês

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