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

作者: Chiaki Kuroda , Takeshi Sunakawa , Yuichi Muguruma

DOI: 10.1002/HLCA.200890093

关键词:

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

参考文章(33)
Ian Fleming, Asuncion Barbero, David Walter, Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds Chemical Reviews. ,vol. 97, pp. 2063- 2192 ,(1997) , 10.1021/CR941074U
Chiaki Kuroda, Masatoshi Okada, Shinya Shinozaki, Hideyuki Suzuki, Self-cyclization of (E)-2-(trimethylsilylmethyl)pentadienol derivative. Synthesis of bicyclo[4.3.0]nonane ring systems Tetrahedron. ,vol. 62, pp. 726- 730 ,(2006) , 10.1016/J.TET.2005.09.146
Raymond J. Giguere, Scott M. Duncan, Joseph M. Bean, Leslie Purvis, Intramolecular [3+4] allyl cation cycloaddition: Novel route to hydroazulenes Tetrahedron Letters. ,vol. 29, pp. 6071- 6073 ,(1988) , 10.1016/S0040-4039(00)82267-4
Chiaki Kuroda, Naoko Mitsumata, Chen Ying Tang, An Acylative C-C Single-Bond Cleavage and a Self-Cyclization of Ethyl 2-(Trimethylsilylmethyl)penta-2,4-dienoate or Its Free Acid under Ritter Condition Bulletin of the Chemical Society of Japan. ,vol. 69, pp. 1409- 1416 ,(1996) , 10.1246/BCSJ.69.1409
Hideyuki Suzuki, Soichi Ohta, Chiaki Kuroda, Synthesis of γ‐Substituted‐β‐(Ethoxycarbonyl)allylsilanes via Peterson Olefination Synthetic Communications. ,vol. 34, pp. 1383- 1392 ,(2004) , 10.1081/SCC-120030687
Chiaki Kuroda, Kenichi Kobayashi, Akira Koito, Shuzo Anzai, Intramolecular Cyclization of (2-Functionalized Allyl)trimethylsilane with Acid Chloride. Synthesis of Two Guaianolide-Type α-Methylene γ-Lactones Bulletin of the Chemical Society of Japan. ,vol. 74, pp. 1947- 1961 ,(2001) , 10.1246/BCSJ.74.1947