326591-72-4Relevant academic research and scientific papers
Reaction of cyclohexanone benzylimines with ethylidenemalonate diesters. Diphenyl 2-ethylidenemalonate: A highly electrophilic synthetic equivalent of crotonic esters
Jabin,Revial,Monnier-Benoit,Netchitailo
, p. 256 - 261 (2001)
The diastereoselective Michael alkylation of α-substituted and α,α′-disubstituted cyclohexanone benzylimines with ethylidenemalonate diesters was carried out for mechanistic and synthetic purposes. In the first case, an reverse regioselectivity occurred m comparison with what is generally observed since the Michael adducts resulted from alkylation of the non substituted enamine tautomer. With α,α′-disubstituted imines, in all cases, the stereochemistry of the major diastereomer the one anticipated from a mechanism including a chairlike complex approach with a preferred was exo position for the β-methyl group of the ethylidenemalonic acid diesters. Furthermore, diphenyl 2-ethylidenemalonate 4 was found to be a highly electrophilic synthetic equivalent of crotonic esters.
A simple and direct access to ethylidene malonates
Sylla, Maite,Joseph, Delphine,Chevallier, Emilie,Camara, Cheikhou,Dumas, Francoise
, p. 1045 - 1049 (2007/10/03)
The condensation of active methylene compounds 1 with acetaldehyde was efficiently promoted by a catalytic amount of lithium bromide in the presence of acetic anhydride to give ethylidene malonates 2 in 77-97% yield. Georg Thieme Verlag Stuttgart.
