2024-03-28T22:53:35Z
https://soar-ir.repo.nii.ac.jp/oai
oai:soar-ir.repo.nii.ac.jp:00011727
2022-12-14T04:11:19Z
1169:1170
Synthesis of a Novel Non-Benzenoid Quinone, 3,10-Dihydro-2,4-dimethyl-7,13-methanocyclohepta[11]annulene-3,10-dione, from 8H-7,9-Bis(methoxycarbonyl)-5,11-methano[11]annuleno[c]furan-8-one
Kuroda, Shigeyasu
Matsumoto, Naoko
Zhang, Yanmei
Miyatake, Ryuta
Fujiwara, Yurie
Oda, Mitsunori
Copyright© 2013 The Japan Institute of Heterocyclic Chemistry
Methano[11]annulene
Furan
Dicationic Species
[4+3] Cycloaddition
Protonation
8H-7,9-Bis(methoxycarbonyl)-5,11-methano[11]anuleno[c]furan-8-one (3) undergoes [4+3] cycloaddition with an oxyallyl species generated from 2,4-dibromo-3-pentanone in the presence of KI and copper, followed by dehydration in fluorosulfuric acid to give cyclohepta[11]annulenedione diester 9. After hydrolysis of the ester groups, decarboxylation yielded the title quinone 6. The H-1 NMR spectrum of 6 in D2SO4 indicates generation of its protonated dicationic species.
Article
HETEROCYCLES. 86(2):1541-1547 (2012)
PERGAMON-ELSEVIER SCIENCE LTD
2013
eng
journal article
AM
http://hdl.handle.net/10091/17269
https://soar-ir.repo.nii.ac.jp/records/11727
https://doi.org/10.3987/COM-12-S(N)75
10.3987/COM-12-S(N)75
0385-5414
AA00663739
HETEROCYCLES
86
2
1541
1547
https://soar-ir.repo.nii.ac.jp/record/11727/files/COM-12-S(N)75.pdf
application/pdf
518.1 kB
2015-09-28