Pregled bibliografske jedinice broj: 196367
Synthesis and chemistry of sesqui-icyclo[2.2.2]octene and a tetradecacyclic-caged sesquibicyclo[2.2.2]octene
Synthesis and chemistry of sesqui-icyclo[2.2.2]octene and a tetradecacyclic-caged sesquibicyclo[2.2.2]octene // Tetrahedron letters, 39 (1998), 44; 8055-8058 (međunarodna recenzija, članak, znanstveni)
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Naslov
Synthesis and chemistry of sesqui-icyclo[2.2.2]octene and a tetradecacyclic-caged sesquibicyclo[2.2.2]octene
Autori
Marchand, A.P. ; Alihodžić, Sulejman ; Dong, E.Z. ; Bott, S.G.
Izvornik
Tetrahedron letters (0040-4039) 39
(1998), 44;
8055-8058
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
cage compounds; promoted reductive dimerization; pinacols
Sažetak
Cationic rearrangements of functionalized spiro(norbornane-7, 3'-bicyclo[2.2.2]octan-2'-ols) provide synthetic access to two novel polycarbocyclic alkenes, i.e., 5 and 10 (''sesquibicyclo[2.2.2]octene''). X-ray crystallographic analysis of 5 and 10 reveals that each alkene C=C double bond is planar in the crystalline solid. MCPBA promoted epoxidation of 5 produced the corresponding oxirane, 11. Ring opening of the highly labile oxirane moiety in 11 occurred in the presence of mild Lewis acids (e.g., silica gel) or bases (e.g., NaHCO3), thereby affording the corresponding cis-diol, 12. MCPBA promoted epoxidation of 7 afforded the corresponding oxirane, 13. Oxirane 13 proved to be considerably less labile than 11 toward acidic and/or basic media.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
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
