Correlation of hydrolysis and desilylation of 2-[(trimethylsilyl)methyl] acrylate derivatives in aqueous alkali solutions
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.
Kuroda, Chiaki,Sunakawa, Takeshi,Muguruma, Yuichi
scheme or table
p. 888 - 896
(2009/03/11)
Substituent Effect on the Chemical Behaviour of some Carbonyl Compounds and Ketals with 1-Ethoxy-3-Trimethylsilyl-prop-1-yne
In this work, principal component analysis (PCA) was carried out on the basis of property descriptors for a set of carbonyl compounds and ketals.A principal component projection of the points representing the compounds showed that the chemical behaviour of the compounds with 1-ethoxy-3-trimethylsilylprop-1-yne is related to their chemical composition.The obtained structure-chemical behaviour information was used to design a space transition state of the studied reactions.
Zakarya, D.,Rayadh, A.,Samih, M.,Lakhlifi, T.
p. 405 - 408
(2007/10/02)
REACTION DE CYCLOADDITION ENTRE L'ETHOXY-1 TRIMETHYLSILYL-3 PROPYNE-1 ET LES ACETALS : SYNTHESE DE CARBETHOXY-2 TRIMETHYLSILANES ALLYLIQUES, DIENIQUES OU ENYNIQUES DIVERSEMENT SUBSTITUES
In the presence of titanium tetrachloride, 1-ethoxy-3-trimethylsilyl-1-propyne easily reacts with many saturated, unsaturated or functional acetals to lead to 2-carbethoxy allylic, dienic or enynic trimethylsilanes, in a regioselective and often stereoselective way.
Pornet, J.,Rayadh, A.,Miginiac, L.
p. 5479 - 5482
(2007/10/02)
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