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Pregled bibliografske jedinice broj: 329502

An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles


Peša, Nela; Welch, Chris J.; Boa, Andrew N.
An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles // Journal of Heterocyclic Chemistry, 42 (2005), 4; 599-607 (međunarodna recenzija, članak, znanstveni)


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Naslov
An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles

Autori
Peša, Nela ; Welch, Chris J. ; Boa, Andrew N.

Izvornik
Journal of Heterocyclic Chemistry (0022-152X) 42 (2005), 4; 599-607

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

Ključne riječi
1; 3-Dipolar cycloaddition reactions; Nitrile oxides; Asymmetric synthesis; Regioselectivity; Rearrangement; Derivatives; Oxidation; Chemistry; Sulfides; Acid

Sažetak
A simple reaction affording (E)-1-dimethylamino-2-phenylsulfonylethylene, and S-((E)-2-(N', N'-dimethylamino)ethenyl)-S-phenyl-N-(p-tolylsulfonyl) sulfoximide in high yields is described. A reversal in regioselectivity was observed when the beta-dimethylaminovinyl sulfone was employed as a dipolarophile in cycloadditions with nitrile oxides. The sulfone gives rise mainly to 4-substituted isoxazoles, after elimination of dimethyl amine. In comparison, phenyl vinyl sulfone cycloadds to give 5-substituted isoxazolines. Although not showing comparable dipolarophilic activity in reactions with nitrile oxides and nitrile imides, the beta-dimethylaminovinyl sulfoximide was easily converted to S-((E)-(3-ethoxycarbonyl)prop-2-enyl)-S-phenyl-N-(p-tolylsulfonyl) sulfoximide. This allylic sulfoximide cycloadds in good yield to both benzonitrile oxide and diphenylnitrile imide, but no stereoselectivity was observed in the process ; and only modest regioselectivity was detected in the case of benzonitrile oxide.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Sveučilište u Osijeku - Odjel za kemiju

Profili:

Avatar Url Nela Malatesti (autor)


Citiraj ovu publikaciju:

Peša, Nela; Welch, Chris J.; Boa, Andrew N.
An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles // Journal of Heterocyclic Chemistry, 42 (2005), 4; 599-607 (međunarodna recenzija, članak, znanstveni)
Peša, N., Welch, C. & Boa, A. (2005) An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles. Journal of Heterocyclic Chemistry, 42 (4), 599-607.
@article{article, year = {2005}, pages = {599-607}, keywords = {1, 3-Dipolar cycloaddition reactions, Nitrile oxides, Asymmetric synthesis, Regioselectivity, Rearrangement, Derivatives, Oxidation, Chemistry, Sulfides, Acid}, journal = {Journal of Heterocyclic Chemistry}, volume = {42}, number = {4}, issn = {0022-152X}, title = {An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles}, keyword = {1, 3-Dipolar cycloaddition reactions, Nitrile oxides, Asymmetric synthesis, Regioselectivity, Rearrangement, Derivatives, Oxidation, Chemistry, Sulfides, Acid} }
@article{article, year = {2005}, pages = {599-607}, keywords = {1, 3-Dipolar cycloaddition reactions, Nitrile oxides, Asymmetric synthesis, Regioselectivity, Rearrangement, Derivatives, Oxidation, Chemistry, Sulfides, Acid}, journal = {Journal of Heterocyclic Chemistry}, volume = {42}, number = {4}, issn = {0022-152X}, title = {An efficient preparation of beta-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles}, keyword = {1, 3-Dipolar cycloaddition reactions, Nitrile oxides, Asymmetric synthesis, Regioselectivity, Rearrangement, Derivatives, Oxidation, Chemistry, Sulfides, Acid} }

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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