Reaction of alpha-ethoxyacrolein with diethyl malonate

Authors
Keiko, NA Chuvashev, YA Kuznetsova, TA Sherstyannikova, LV Voronkov, MG
Citation
Na. Keiko et al., Reaction of alpha-ethoxyacrolein with diethyl malonate, RUSS CHEM B, 47(12), 1998, pp. 2426-2428
Citations number
14
Categorie Soggetti
Chemistry
Journal title
RUSSIAN CHEMICAL BULLETIN
ISSN journal
10665285 → ACNP
Volume
47
Issue
12
Year of publication
1998
Pages
2426 - 2428
Database
ISI
SICI code
1066-5285(199812)47:12<2426:ROAWDM>2.0.ZU;2-#
Abstract
The reaction of alpha-ethoxyacrolein with diethyl malonate in the presence of EtONa, lithium diisopropylamide, or the Na2CO3-benzene-Et-3(PhCH2)NCl ca talytic system proceeds as the Michael addition. In the presence of an equi molar amount of triethylamine, selective 1,2-addition followed by dehydrati on of the 1,2-adduct occurs. Owing to the strong +M effect of the EtO group , alpha-ethoxyacrolein is a substantially less active Michael acceptor than acrolein.