THE REACTION OF AN ALPHA-OXOPHOSPHONIUM YLIDE WITH HALOGENS - 2,3-DISUBSTITUTED DIETHYL BUTENEDIOATES FROM DIETHYL 2-OXO-3-TRIPHENYLPHOSPHORANYLIDENEBUTANEDIOATE

Authors
GONSALVES AMDR CABRAL AMTDPV MELO TMVDPE GILCHRIST TL
Citation
Amdr. Gonsalves et al., THE REACTION OF AN ALPHA-OXOPHOSPHONIUM YLIDE WITH HALOGENS - 2,3-DISUBSTITUTED DIETHYL BUTENEDIOATES FROM DIETHYL 2-OXO-3-TRIPHENYLPHOSPHORANYLIDENEBUTANEDIOATE, Synthesis, (6), 1997, pp. 673
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
6
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):6<673:TROAAY>2.0.ZU;2-I
Abstract
The title ylide I reacts with chlorine and with bromine in the presenc e of a range of nucleophiles. Triphenylphosphine oxide is eliminated a nd 2,3-disubstituted ethyl butenedioates 2-5 are isolated in moderate to good yield. The structure of one product, diethyl (2)-2-acetoxy-3-b romobutenedioate (3 a), has been established by X-ray crystallography. Similar reactions between the ylide 1 and N-bromo-succinimide and N-c hlorosuccinimide in methanol or in the presence of azidotrimethylsilan e give the diesters 6-8. Several of the reactions are highly stereosel ective whereas others give both (E)- and (Z)-isomers.