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

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