Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph3P, AcS-, CN-, I -, F-, Ac
Baranac-Stojanovi?, Marija,Tatar, Jovana,Stojanovi?, Milovan,Markovi?, Rade
experimental part
p. 6873 - 6884
(2010/10/01)
Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives
Regioselective α-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxothiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed.
Markovi?, Rade,D?ambaski, Zdravko,Baranac, Marija
p. 5833 - 5841
(2007/10/03)
Regioselective synthesis of new 5-ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene bromides and rearrangement reaction thereof
(Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a-c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a-c. They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a-c to 5a-c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a-c. Thieme Stuttgart.
Markovi?, Rade,Baranac, Marija
p. 607 - 610
(2007/10/03)
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