Serendipity in Action: Functionalized Acrylates and Methacrylates

摘要

Methacrylic esters functionalized on the alpha-methyl radical provide a family of monomers with a wide range of further derivatives and polymerizability. One step synthesis of the alphahydroxymethyl esters from acrylate esters and paraformaldehyde provides an inexpensive entry to these monomers. Surprisingly facile base-catalyzed dimerization give ether-lined diacrylates capable of cyclopolymerization or crosslinking. The alcohol group is also easily reacted to give polymerizable ester, silyloxy, urethane, and ether monomers. Quantitative conversion to the chloro-compound gives a highly reactive homo- and comonomer, and further provides a mild pathway to additional ether, amine, ammonium, and thioether polymer derivatives via monomers or reaction on preformed chloromethyl polymers. WARNING: Some of these monomers are powerful skin irritants and must be handled carefully. Reprints. (AW)