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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), 3; 408-416 doi:10.1016/j.jfluchem.2009.12.012 (međunarodna recenzija, članak, znanstveni)

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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), 3; 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

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

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Davor Margetić (autor)

Avatar Url Mirjana Maksić (autor)

Avatar Url Pavle Trošelj (autor)

Avatar Url Željko Marinić (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com doi.org

Citiraj ovu publikaciju:

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), 3; 408-416 doi:10.1016/j.jfluchem.2009.12.012 (međunarodna recenzija, članak, znanstveni)
Margetić, D., Eckert-Maksić, M., Trošelj, P. & Marinić, Ž. (2010) 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 (3), 408-416 doi:10.1016/j.jfluchem.2009.12.012.
@article{article, author = {Margeti\'{c}, Davor and Eckert-Maksi\'{c}, Mirjana and Tro\v{s}elj, Pavle and Marini\'{c}, \v{Z}eljko}, year = {2010}, pages = {408-416}, DOI = {10.1016/j.jfluchem.2009.12.012}, keywords = {Diels-Alder reaction, 1, 3-dipolar cycloaddition, oxadiazoles, norbornenes, reaction mechanism, calculations}, journal = {Journal of fluorine chemistry}, doi = {10.1016/j.jfluchem.2009.12.012}, volume = {131}, number = {3}, issn = {0022-1139}, title = {Reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7- oxanorbornenes revisited: experimental and quantum-chemical study of reaction stereospecificity}, keyword = {Diels-Alder reaction, 1, 3-dipolar cycloaddition, oxadiazoles, norbornenes, reaction mechanism, calculations} }
@article{article, author = {Margeti\'{c}, Davor and Eckert-Maksi\'{c}, Mirjana and Tro\v{s}elj, Pavle and Marini\'{c}, \v{Z}eljko}, year = {2010}, pages = {408-416}, DOI = {10.1016/j.jfluchem.2009.12.012}, keywords = {Diels-Alder reaction, 1, 3-dipolar cycloaddition, oxadiazoles, norbornenes, reaction mechanism, calculations}, journal = {Journal of fluorine chemistry}, doi = {10.1016/j.jfluchem.2009.12.012}, volume = {131}, number = {3}, issn = {0022-1139}, title = {Reaction of 2, 5-bis-trifluoromethyl-1, 3, 4-oxadiazole with 7- oxanorbornenes revisited: experimental and quantum-chemical study of reaction stereospecificity}, keyword = {Diels-Alder reaction, 1, 3-dipolar cycloaddition, oxadiazoles, norbornenes, reaction mechanism, calculations} }

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

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