3061-65-2Relevant academic research and scientific papers
A Formylcarbonium Ion Synthon. Synthesis of 3-Thio-Substituted 2-Amino Acids and Thio-Substituted Enamines from 2-Acyloxyacrylonitriles
Oku, Akira,Hori-ie, Naofumi,Harada, Toshiro
, p. 609 - 612 (2007/10/02)
The utilization of 2-acyloxy-3-phenylthiopropionitriles (2) which were prepared by the Michael addition of thiophenol to 2-acyloxyacrylonitriles (CH2=C(CN)OCOR), as a formylcarbonium ion synthon, was demonstrated by the transformation of 2 into S-phenylcysteine and 2-phenylthio enamines.
Trimethylsilyl Cyanide - A Reagent for Umpolung, VIII. Derivatives of 2-(Trimethylsilyloxy)-2-propenenitrile. Syntheses and General Properties
Hertenstein, Ulrich,Huenig, Siegfried,Reichelt, Helmut,Schaller, Rainer
, p. 261 - 287 (2007/10/02)
Rather different derivatives of the new title compuond 7 were synthesized by routes A - H (Table 2 and 3).The effects of substituents and reaction routes on the E/Z ratios (NMR) is discussed.Replacement of SiMe3 in 7 by RCO- and MeSO2- yields other alkenes with donor (O - X) and acceptor groups (CN) at the same C-atom.Their opposite effects on the β-C-atom is estimated from the corresponding 1H- and 13C-NMR signals.
Preparing carboxylic acids from glycidonitriles through enol acylates
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, (2008/06/13)
Process for preparing carboxylic acids by converting a glycidonitrile to the enol acylate via hydrohalogenation, acylation and dehydrohalogenation procedures, and conversion of the enol acylate to the carboxylate salt with a base and of the salt to the carboxylic acid with acid. Cyanide content in the mixture is destroyed by adding persulfate or hypochlorite salts. This process, can be used, e.g., to prepare 2-(4'-isobutylphenyl)propionic acid, now known generically as ibuprofen, a highly active anti-inflammatory drug, as well as a host of other useful carboxylic acids.
