Correlation of Hydrolysis and Desilylation of 2-[(Trimethylsilyl)methyl]acrylate Derivatives in Aqueous Alkali Solutions

✍ Scribed by Chiaki Kuroda; Takeshi Sunakawa; Yuichi Muguruma

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 195 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890093

✦ Synopsis

Abstract

Hydrolysis and desilylation reaction of 2‐[(trimethylsilyl)methyl]acrylate (=2‐[(trimethylsilyl)methyl]prop‐2‐enoate) derivatives were studied to evaluate the effect of the presence/absence of a further conjugating substituent (Schemes 3 and 4 and Tables 1 and 2). The substrates having a nonconjugating substituent at the acrylate moiety were stable to dilute alkali conditions, and afforded simple hydrolysis products under concentrated alkali conditions. In contrast, both hydrolysis and desilylation occurred from the substrates bearing conjugated substituents at the acrylate skeleton. The difference in reactivity can be explained in terms of the stabilization of the intermediate anion.