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Titolo:
Efficient preparation of monoadducts of [60]fullerene and anthracenes by solution chemistry and their thermolytic decomposition in the solid state
Autore:
Krautler, B; Muller, T; Duarte-Ruiz, A;
Indirizzi:
Innsbruck Univ, Inst Organ Chem, A-6020 Innsbruck, Austria Innsbruck UnivInnsbruck Austria A-6020 Chem, A-6020 Innsbruck, Austria
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 15, volume: 7, anno: 2001,
pagine: 3223 - 3235
SICI:
0947-6539(20010803)7:15<3223:EPOMO[>2.0.ZU;2-I
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIELS-ALDER REACTIONS; DIRECTED REMOTE FUNCTIONALIZATION; BUCKMINSTERFULLERENE C-60; FULLERENE CHEMISTRY; METAL-COMPLEXES; T-H; ADDUCT; CARBON; CYCLOPENTADIENE; CYCLOADDITIONS;
Keywords:
cycloaddition; Diels-Alder reactions; fullerenes; solid-state reactions; topochemistry;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
71
Recensione:
Indirizzi per estratti:
Indirizzo: Krautler, B Innsbruck Univ, Inst Organ Chem, Innrain 52A, A-6020 Innsbruck, Austria Innsbruck Univ Innrain 52A Innsbruck Austria A-6020 , Austria
Citazione:
B. Krautler et al., "Efficient preparation of monoadducts of [60]fullerene and anthracenes by solution chemistry and their thermolytic decomposition in the solid state", CHEM-EUR J, 7(15), 2001, pp. 3223-3235

Abstract

The efficient preparation of monoadducts of [60]fullerene and seven anthracenes (anthracene, 1-methylanthracene, 2-methylanthracene, 9-methylanthracene, 9,10-dimethylanthracene, 2,3,6,7-tetramethylanthracene, and 2,6-di-tert-butylanthracene) by cycloaddition in solution is described. The seven mono-adducts of [60]fullerene and the anthracenes were characterized spectroscopically and were obtained in good yields as crystalline solids. The monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 2-methylanthracene and 9,10-dimethylanthracene crystallized directly from the reaction mixture. The thermolytic decomposition at 180 degreesC of the crystalline monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 9-methylanthracene and 9,10-dimethylanthracene all gave rise to the specific formation of aroughly 1:1 mixture of [60]fullerene and the corresponding antipodal bisadducts ("trans-1"-bisadducts) of [60]fullerene and the anthracenes. In contrast, the crystalline monoadducts of [60]fullerene and the anthracene derivatives 2-methylanthracene, 2,3,6,7-tetramethylanthracene and 2,6-di-tert-butylanthracene all decomposed to [60]fullerene and anthracenes (without detectable formation of bisadducts) upon heating in the solid state to temperatures of 180 to 240 degreesC. The formation of the antipodal bisadducts from thermolytic decomposition of crystalline samples of the monoadducts was rationalized by topochemical control.

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Documento generato il 03/07/20 alle ore 01:13:21