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- Title
Reactions of Perylene with Aryne Intermediates.
- Authors
Pavlyuk, D. E.; Gundala, S.; Kovalev, I. S.; Kopchuk, D. S.; Krinochkin, A. P.; Budeev, A. V.; Zyryanov, G. V.; Venkatapuram, P.; Rusinov, V. L.; Chupakhin, O. N.
- Abstract
The Diels-Alder reactions of perylene (diene) with 1,2-didehydrobenzene and 4,5-dimethoxy-1,2-didehydrobenzene (dienophiles) generated in situ by two methods were studied. According to the first method, diazonium salts derived from anthranilic acids and stabilized by 4-dodecylbenzenesulfonic acid were treated with potassium fluoride in toluene in the presence of 18-crown-6 on heating. The second method involved generation of arynes directly from substituted anthranilic acids by the action of isoamyl nitrite in toluene on heating. The corresponding Diels-Alder adducts, naphtho[1,2,3,4-ghi]perylene and 10,11-dimethoxynaphtho-[1,2,3,4-ghi]perylene, were isolated in up to 77% yield. The yield was higher when the aryne intermediate was generated from the stabilized diazonium salts. 4,5-Difluoro-1,2-dehydrobenzene and 2,3-dehydronaphthalene generated by both methods failed to react with perylene.
- Subjects
PERYLENE; ARYNE; DIAZONIUM compounds; AMINOBENZOIC acids; POTASSIUM fluoride; DIELS-Alder reaction
- Publication
Russian Journal of Organic Chemistry, 2019, Vol 55, Issue 3, p409
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428019030278