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Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study


Picek, Igor; Vianello, Robert; Šket, Primož; Plavec, Janez; Foretić, Blaženka
Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study // Journal of organic chemistry, 80 (2015), 4; 2165-2173 doi:10.1021/jo5026755 (međunarodna recenzija, članak, znanstveni)


Naslov
Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study

Autori
Picek, Igor ; Vianello, Robert ; Šket, Primož ; Plavec, Janez ; Foretić, Blaženka

Izvornik
Journal of organic chemistry (0022-3263) 80 (2015), 4; 2165-2173

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

Ključne riječi
Tandem reactions; Pyridine oxime ether; Reaction mechanisms; Rearrangement

Sažetak
A novel OH−-promoted tandem reaction involving C(β)–N+(pyridinium) cleavage and ether C(β)–O(oxime) bond formation in aqueous media has been presented. The study fully elucidates the fascinating reaction behavior of N-benzoylethylpyridinium-4-oxime chloride inaqueous media under mild reaction conditions. The reaction journey begins with the exclusive β- elimination and formation of pyridine-4-oxime and phenyl vinyl ketone and ends with the formation of O-alkylated pyridine oxime ether. A combination of experimental and computational studies enabled the introduction of the new type of rearrangement process that involves a unique tandem reaction sequence. We showed that O-benzoylethylpyridine-4-oxime ether is formed in aqueous solution by a base-induced tandem β-elimination/hetero-Michael addition rearrangement of N-benzoylethylpyridinium-4-oximate, the novel synthetic route to this engaging target class of compounds. The complete mechanistic picture of this rearrangement process was presented and discussed in terms of the E1cb reaction scheme within the rate limiting β-elimination step.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2932 - Broenstedove i Lewisove kiseline i baze u kemiji i biokemiji (Robert Vianello, )
108-1193079-3070 - Kompleksi željeza i biološki aktivnih liganada (Blaženka Foretić, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Medicinski fakultet, Zagreb

Profili:

Avatar Url Blaženka Foretić (autor)

Avatar Url Igor Picek (autor)

Avatar Url Robert Vianello (autor)

Citiraj ovu publikaciju

Picek, Igor; Vianello, Robert; Šket, Primož; Plavec, Janez; Foretić, Blaženka
Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study // Journal of organic chemistry, 80 (2015), 4; 2165-2173 doi:10.1021/jo5026755 (međunarodna recenzija, članak, znanstveni)
Picek, I., Vianello, R., Šket, P., Plavec, J. & Foretić, B. (2015) Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study. Journal of organic chemistry, 80 (4), 2165-2173 doi:10.1021/jo5026755.
@article{article, year = {2015}, pages = {2165-2173}, DOI = {10.1021/jo5026755}, keywords = {Tandem reactions, Pyridine oxime ether, Reaction mechanisms, Rearrangement}, journal = {Journal of organic chemistry}, doi = {10.1021/jo5026755}, volume = {80}, number = {4}, issn = {0022-3263}, title = {Tandem β-Elimination/hetero-Michael Addition Rearrangement of the N-Alkylated Pyridinium Oxime to O-Alkylated Pyridine Oxime Ether : An Experimental and Computational Study}, keyword = {Tandem reactions, Pyridine oxime ether, Reaction mechanisms, 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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