Specific features of the chemical behavior of acetylenic derivatives of benzocrown ethers

S. V. Klyatskaya, E. V. Tretyakov, S. F. Vasilevsky

Результат исследований: Материалы для журналаСтатья

5 Цитирования (Scopus)

Выдержка

4′-Ethynylbenzo-12-crown-4 (8), 4′-ethynylbenzo-15-crown-5 (9), and 4′-ethynylbenzo-18-crown-6 (10) were synthesized by cross-coupling of the corresponding aryl iodides 1-3 with 2-methylbut-3-yn-2-ol (4a) followed by the retro-Favorsky cleavage of the resulting carbinols. Unlike the corresponding benzo-12-crown-4 derivative (5a), the cleavage of tertiary acetylenic alcohols of benzo-15-crown-5 (6a) and benzo-18-crown-6 (7a) requires more than one molar equivalent of KOH. Aminoalkylation of crown ether 8 gives Mannich bases, independently of the reaction conditions and the nature of amine. The aminomethylation of acetylenic crown ethers 9 and 10 with paraform-piperidine (morpholine) in the presence of CuCl yields 1,4-disubstituted buta-1,3-diynes (19, 20) rather than Mannich bases.

Язык оригиналаАнглийский
Страницы (с-по)868-873
Число страниц6
ЖурналRussian Chemical Bulletin
Том50
Номер выпуска5
DOI
СостояниеОпубликовано - 1 дек 2001
Опубликовано для внешнего пользованияДа

Отпечаток

Mannich Bases
Crown Ethers
Ethers
Diynes
Derivatives
Iodides
Amines
Methanol
12-crown-4
15-crown-5
18-crown-6

ASJC Scopus subject areas

  • Chemistry(all)

Цитировать

Specific features of the chemical behavior of acetylenic derivatives of benzocrown ethers. / Klyatskaya, S. V.; Tretyakov, E. V.; Vasilevsky, S. F.

В: Russian Chemical Bulletin, Том 50, № 5, 01.12.2001, стр. 868-873.

Результат исследований: Материалы для журналаСтатья

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AU - Vasilevsky, S. F.

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KW - Alkynes

KW - Benzocrown ethers

KW - Crown effect

KW - Frank-Meister-Hay modification

KW - The Mannich reaction

KW - The retro-Favorsky reaction

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