Synthesis of Distorted 1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates to 3-Silylbenzynes.
arynes
distortion
regioselectivity
triptycene
ynolate
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
04 Nov 2019
04 Nov 2019
Historique:
received:
02
07
2019
revised:
22
07
2019
pubmed:
25
7
2019
medline:
25
7
2019
entrez:
24
7
2019
Statut:
ppublish
Résumé
1,8,13-Trialkyl(aryl)silyl-9-hydroxytriptycenes (trisilyltriptycenes) were synthesized by the triple addition of ynolates and 3-silylbenzynes with high regioselectivity. Benzene rings in the resulting triptycenes were highly distorted where the dihedral angles between the substituents were as high as 35°. The distortion energy induced step-by-step halogenation reactions to yield halogenated triptycenes, including chiral triptycenes. The 1,8,13-trihalogenated triptycenes were then converted to 1,8,13-functionalized triptycenes.
Identifiants
pubmed: 31334876
doi: 10.1002/chem.201903024
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13855-13859Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP18H02557
Organisme : Japan Society for the Promotion of Science
ID : JP18H04418
Organisme : Japan Society for the Promotion of Science
ID : JP18H04624
Organisme : Japan Society for the Promotion of Science
ID : JP17K14449
Organisme : Asahi Glass Foundation
Organisme : Ministry of Education, Culture, Sports, Science and Technology
ID : "Integrated Research Consortium on Chemical Sciences
Organisme : Asahi Glass Foundation
ID : 0000
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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