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Synthesis of Oligo(isobutyl vinyl ether) with a Silyl Enol Ether End Group and their Aldol Reactions with Benzaldehyde
Author(s) -
Sarker Prodip K.,
Rimmer Stephen
Publication year - 2005
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200500128
Subject(s) - benzaldehyde , silylation , aldol reaction , chemistry , silyl enol ether , vinyl ether , ether , enol ether , cationic polymerization , silyl ether , enol , polymer chemistry , organic chemistry , ketone , medicinal chemistry , copolymer , catalysis , polymer
Summary: Cationic polymerizations of isobutyl vinyl ether ( i BVE) were carried out in the presence of a difunctional silyl enol ether, 3,3‐dimethylpent‐2,4‐(trimethylsilyloxy)‐1,4‐diene. This procedure gave oligomers with silyl enol ether end groups. The silyl enol ether groups reacted in Lewis acid mediated aldol reactions with benzaldehyde to give predominately the β ‐hydroxy ketone product at the chain end. Benzaldehyde could be added either prior to initiation ( ab initio methodology) or at a time after the propagation of i BVE had completed (sequential methodology). The ab initio methodology was shown to produce similar materials to the sequential method but the latter required higher reaction temperatures.