SELECTED REACTION OF (Z)-DIMETHYL ALPHA-(BROMOMETHYL) FUMARATE WITH SECONDARY-AMINES

Authors
BENGHARBIA S BESBES R VILLIERAS J AMRI H
Citation
S. Bengharbia et al., SELECTED REACTION OF (Z)-DIMETHYL ALPHA-(BROMOMETHYL) FUMARATE WITH SECONDARY-AMINES, Synthetic communications, 26(9), 1996, pp. 1685-1692
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
26
Issue
9
Year of publication
1996
Pages
1685 - 1692
Database
ISI
SICI code
0039-7911(1996)26:9<1685:SRO(AF>2.0.ZU;2-P
Abstract
Regioselective reaction of (Z)-dimethyl alpha-(bromomethyl) fumarate 2 with bulky secondary amines in ether as solvent at room temperature, leads exclusively to the rearranged substitution alpha-(functional alk yl amino) acrylic esters 4a-i in high yields. The less and more bulky amine gives rise respectively to the two successive (S(N)2') and (S(N) 2) substitution derivatives 5j,k and 51.