1,3-BUTADIENE-1-CARBOXYLIC ACID METHYL ESTER

1,3-BUTADIENE-1-CARBOXYLIC ACID METHYL ESTER is used as a electron-poor diene capable of cycloaddition reactions with activated dienophiles to form carbocyclic and heterocyclic compounds; metal-promoted [6 + 4] cycloadditions and metal-promoted chain extensions.

1,3-BUTADIENE-1-CARBOXYLIC ACID METHYL ESTER is prepared by Wittig alkenation of Acrolein with (Methoxycarbonylmethylene)triphenylphosphorane; reaction of Malonic Acid with acrolein, followed by esterification.

Journal of the American Chemical Society, 94, p. 4395, 1972 DOI: 10.1021/ja00767a088
Synthesis, p. 534, 1988 DOI: 10.1055/s-1988-27626

Methyl 2,4-pentadienoate undergoes Aza-Morita-Baylis-Hillman reaction with aldimines in DMF in the presence of 3-hydroxyquinuclidine.

Polymerizes easily.