108833-85-8Relevant articles and documents
ISOLEMENT DU "REACTIF DE REFORMATSKY" DERIVE DE L'α-(BROMOMETHYL) ACRYLATE D'ETHYLE
Alami, N. E.,Belaud, C.,Villieras, J.
, p. 59 - 60 (1987)
The organozinc reagent derived from ethyl α-(bromomethyl) acrylate is prepared at 17 deg C T 20 deg C (duplication 10percent) and then coupled efficiently with nucleophilic imines to give α-methylene γ-lactames with high yields.
Reactivite de l'organozincique derive de l'α-bromomethyl acrylate d'ethyle
Alami, N. El.,Belaud, C.,Villieras, J.
, p. 157 - 168 (2007/10/02)
The organozinc derivative (2a) of ethyl α-bromomethyl acrylate is not nucleophilic towards haloalkanes but can be alkylated with chlorotrimethylsilane. 2a is unreactive towards carbon-oxygen single bonds and is unsuitable for conjugate addition (α-enones and α,β-ethylenic esters).Its acylation can be carried out in DME in the presence of palladium(0) catalyst.Reactions with carbon-oxygen and and carbon-nitrogen double bonds permit the preparation of α-methylene γ-butyrolactones and lactams without the formation of side-products.This route is especially suitable for reactions with substrates such as imines that are both nucle ophilic and electrophilic.