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Pregled bibliografske jedinice broj: 639676

Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack

Shang, Muhong; Butler, Douglas N.; Warrener, Ronald N.; Margetić, Davor
Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack // Tetrahedron letters, 54 (2013), 39; 5335-5339 doi:10.1016/j.tetlet.2013.07.105 (međunarodna recenzija, članak, znanstveni)

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Naslov
Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack

Autori
Shang, Muhong ; Butler, Douglas N. ; Warrener, Ronald N. ; Margetić, Davor

Izvornik
Tetrahedron letters (0040-4039) 54 (2013), 39; 5335-5339

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

Ključne riječi
Retro-Diels–Alder; pyrolysis; oxepines; molecular racks; rearrangement

Sažetak
The thermal rearrangement of [3]polynorbornane bis-imide rack-mounted 7-oxabenzonorbornadienes has been conducted using flash vacuum pyrolysis (FVP) at 520 C and is compared with the FVP of similar 7-oxabenzonorbornadienes off the rack. The isomerisation is considered to involve (a) C–O bond cleavage to a vinylogous 1, 5-dipole, (b) formation of a benzene epoxide by nucleophilic ring-closure and (c) valence-isomerisation of the benzene epoxide to the oxepine. Competing fragmentation to the isobenzofuran by ejection of acetylene and other rearrangements become prominent pathways off the rack, whereas isomerisation to the oxepine is highly favored on the rack.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA

Projekti:
098-0982933-3218 - Host-guest međudjelovanja u policikličkim sustavima (Margetić, Davor, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Davor Margetić (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com ac.els-cdn.com dx.doi.org

Citiraj ovu publikaciju:

Shang, Muhong; Butler, Douglas N.; Warrener, Ronald N.; Margetić, Davor
Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack // Tetrahedron letters, 54 (2013), 39; 5335-5339 doi:10.1016/j.tetlet.2013.07.105 (međunarodna recenzija, članak, znanstveni)
Shang, M., Butler, D., Warrener, R. & Margetić, D. (2013) Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack. Tetrahedron letters, 54 (39), 5335-5339 doi:10.1016/j.tetlet.2013.07.105.
@article{article, author = {Shang, Muhong and Butler, Douglas N. and Warrener, Ronald N. and Margeti\'{c}, Davor}, year = {2013}, pages = {5335-5339}, DOI = {10.1016/j.tetlet.2013.07.105}, keywords = {Retro-Diels–Alder, pyrolysis, oxepines, molecular racks, rearrangement}, journal = {Tetrahedron letters}, doi = {10.1016/j.tetlet.2013.07.105}, volume = {54}, number = {39}, issn = {0040-4039}, title = {Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack}, keyword = {Retro-Diels–Alder, pyrolysis, oxepines, molecular racks, rearrangement} }
@article{article, author = {Shang, Muhong and Butler, Douglas N. and Warrener, Ronald N. and Margeti\'{c}, Davor}, year = {2013}, pages = {5335-5339}, DOI = {10.1016/j.tetlet.2013.07.105}, keywords = {Retro-Diels–Alder, pyrolysis, oxepines, molecular racks, rearrangement}, journal = {Tetrahedron letters}, doi = {10.1016/j.tetlet.2013.07.105}, volume = {54}, number = {39}, issn = {0040-4039}, title = {Rack-mounted chemistry IV : the thermal rearrangement of 7-oxabenonorbornadienes into benzo[b]oxepines on and off the polycyclic rack}, keyword = {Retro-Diels–Alder, pyrolysis, oxepines, molecular racks, rearrangement} }

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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