Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

Unusual mode of reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions

The reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions, using Ac2O, TFAA, SOCl2 and SOBr2 as initiators, has been examined. Almost all reactions proceeded with absolute regioselectivity yielding α-substituted sulfides or vinyl-chloro derivatives. The mechani...

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Veröffentlicht in:Tetrahedron 2013-11, Vol.69 (46), p.9819-9825
Hauptverfasser: Dzambaski, Zdravko, Toljic, Dorde, Bondzic, Bojan, Markovic, Rade, Baranac-Stojanovic, Marija
Format: Artikel
Sprache:eng
Schlagworte:
2-Alkylidene-4-oxothiazolidine S-oxide
Density functional calculations
Derivatives
Formations
Initiators
Pummerer reaction
Regioselectivity
Sulfides
Tetrahedrons
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Zusammenfassung:The reactivity of 2-alkylidene-4-oxothiazolidine S-oxides under the Pummerer reaction conditions, using Ac2O, TFAA, SOCl2 and SOBr2 as initiators, has been examined. Almost all reactions proceeded with absolute regioselectivity yielding α-substituted sulfides or vinyl-chloro derivatives. The mechanism for the formation of the latter products was postulated and proved experimentally. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.09.004