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Pregled bibliografske jedinice broj: 439535

Reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7- oxanorbornenes revisited: experimental and quantum-chemical study of reaction stereospecificity


Margetić, Davor; Eckert-Maksić, Mirjana; Trošelj, Pavle; Marinić, Željko
Reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7- oxanorbornenes revisited: experimental and quantum-chemical study of reaction stereospecificity // Journal of fluorine chemistry, 131 (2010), 408-416 (međunarodna recenzija, članak, znanstveni)


Naslov
Reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7- oxanorbornenes revisited: experimental and quantum-chemical study of reaction stereospecificity

Autori
Margetić, Davor ; Eckert-Maksić, Mirjana ; Trošelj, Pavle ; Marinić, Željko

Izvornik
Journal of fluorine chemistry (0022-1139) 131 (2010); 408-416

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Diels-Alder reaction; 1; 3-dipolar cycloaddition; oxadiazoles; norbornenes; reaction mechanism; calculations

Sažetak
The stereochemical outcome of reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7-oxanorbornenes under various conditions was investigated. For the first time, microwave irradiation in carrying this type of reactions was used, resulting in comparable yields in significantly shorter reaction times. Regardless on substrate, in all reactions mixtures of two isomeric O3-[3]polynorbornanes, bent and linear were obtained, with slight preference for bent structure. In some cases, retro Diels-Alder fragmentation was observed resulting in formation of isobenzofuran species. Reaction mechanism was also studied computationally (RHF/6-31G* method), and the origin of stereospecificity explained by repulsive lone pair interactions between oxygen bridges in the transition state of the 1, 3-dipolar addition.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
098-0982933-2920 - Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima (Mirjana Maksić, )
098-0982933-3218 - 'Host-guest' međudjelovanja u policikličkim sustavima (Davor Margetić, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus