Synthesis of Oligo(isobutyl vinyl ether) with a Silyl Enol Ether End Group and their Aldol Reactions with Benzaldehyde

✍ Scribed by Prodip K. Sarker; Stephen Rimmer

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 152 KB
• Volume: 206
• Category: Article
• ISSN: 1022-1352
• DOI: 10.1002/macp.200500128

✦ Synopsis

Abstract

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.
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