Investigations on organozinc compounds XIV. Organozinc-catalyzed polymerization of lactones. The interaction between ethylzinc methoxide and (ethylzinc)diphenylamine and β-propiolactone
article
Ethylzinc methoxide brings about selective acyl-oxygen cleavage of the ring of β-propiolactone to give ethylzinc 2-(methoxycarbonyl)ethoxide. The latter compound, which is pentameric in benzene, has been characterized, as well as the alkyl-oxygen cleavage product ethylzinc 3-methoxypropionate. The isolation of the 2-(methoxycarbonyl)ethyl ester of 3-hydroxypropionic acid suggests that the EtZnOMe-catalyzed polymerization of β-propiolactone proceeds by successive insertion of monomer units into the ZnO bond of the complex between the catalyst and the growing polymer through acyl-oxygen cleavage of the lactone ring. (Ethylzinc)diphenylamine similarly reacts selectively with acyl-oxygen cleavage to give ethylzinc 2-(diphenylcarbamoyl)ethoxide in the 1 1 reaction. This compound readily decomposes with formation of N,N-diphenylacrylamide. © 1970.
TNO Identifier
227182
ISSN
0022328X
Source
Journal of Organometallic Chemistry, 24(2), pp. 257-262.
Pages
257-262
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