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Correlation of Hydrolysis and Desilylation of 2‐[(Trimethylsilyl)methyl]acrylate Derivatives in Aqueous Alkali Solutions
Author(s) -
Kuroda Chiaki,
Sunakawa Takeshi,
Muguruma Yuichi
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890093
Subject(s) - chemistry , trimethylsilyl , hydrolysis , substituent , moiety , alkali metal , methyl acrylate , alkaline hydrolysis , acrylate , reactivity (psychology) , aqueous solution , organic chemistry , medicinal chemistry , polymer chemistry , polymer , medicine , alternative medicine , monomer , pathology , copolymer
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.