SYNTHESIS OF A NOVEL NON-BENZENOID QUINONE, 3,10-DIHYDRO-2,4-DIMETHYL-7,13-METHANOCYCLOHEPTA[11]-AN NULENE-3,10-DIONE, FROM 8H-7,9-BIS(METHOXYCARBONYL)-5,11-METHANO[11]ANNULENO[c]FURAN-8-ONE

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 hy...

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Bibliographic Details
Published inHeterocycles Vol. 86; no. 2; pp. 1541 - 1547
Main Authors Kuroda, Shigeyasu, Matsumoto, Naoko, Zhang, Yanmei, Miyatake, Ryuta, Fujiwara, Yurie, Oda, Mitsunori
Format Journal Article
LanguageEnglish
Published Tokyo Japan Inst Heterocyclic Chemistry 31.12.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Furan
Protonation
Dicationic Species
Methanoannulene
[4+3] Cycloaddition
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Summary: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.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-12-S(N)75